Operator Spotlight: AdRoll President Roli Saxena

“How did they do that? How did they get there?” Companies succeed because of the people who run them — operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game — building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

This month we spoke with Roli Saxena, president of marketing technology company AdRoll and board member at Culture Amp, an employee listening platform.

You’ve had incredible success with high growth companies across a variety of industries and sectors, from LinkedIn to to Brex, and now AdRoll. What’s the thread that pulls them all together? 

ROLI: There are a few common threads across all these experiences. They all were in big markets and solving real pain points for their users. And that’s why they each had strong traction in the market with their flagship product and were transforming into multiproduct companies. They also have hybrid business models with both subscription and usage-based pricing. This not only provides the predictability of a SaaS company but also brings an upside with the ability to ‘land and expand.’ 

Customer success and product usage is a strong revenue growth driver and my experience building that at LinkedIn, along with building customer-centric sales organizations, attracted me to each of these opportunities. In my current role, I bring the same level of customer centricity across product, design, revenue, and marketing.

How did your experience in different functional areas prepare you for a major operating role like President? 

ROLI: I am a business leader with go-to-market (GTM) expertise. My first 7-8 years were in product and more recently I’ve spent 10-12 years in a variety of GTM roles — marketing, sales and success. Each of those transitions were motivated by the opportunity to solve big meaty problems and to learn. As an engineer by training, all these experiences have helped me become a systems level problem solver — addressing the problem at the first principle level. A great benefit of all these changes is that I am not afraid of new challenges or of testing new ideas in a structured way. 

Over the years, I have learned that what scales you as a leader is intellectual curiosity and hiring and developing talent. Your job as a leader is to bring strong leaders around the table, set the direction, and give your team space to go execute to that common goal. The collective power of a team with strong aligned conviction is magical.

Which aspects of finance, product, and marketing are most crucial to nail as AdRoll continues to scale? 

ROLI: AdRoll’s mission is to create a level playing field for ambitious ecommerce brands of all sizes. We built our strength in advertising, data, and machine learning and now offer a multi-channel campaign management and attribution platform that enables marketers to attract, engage, and retain their shoppers all from within the AdRoll platform. We also deliver real-time analytics and insights to marketers to best optimize their marketing budgets. Given where we are in our transformation, we have to nail continued product innovation. We are in a highly competitive space and so velocity of innovation is critical for us to keep our lead and gain share.  

What kind of impact do you want your leadership and work style to have on the teams at Adroll and the company overall? 

ROLI: As an introverted woman of color, I am very focused on building a culture of diversity and inclusion. I am fortunate to be working for a company that has prioritized DEI efforts at all levels, including our Board of Directors where we have three independent members who are women. 

Outside of our culture of inclusion, I am invested in building a culture of rapid decision making and accountability. Companies in our stage often lose their startup agility and speed of execution because of fuzzy lines of accountability and stalled decisions. We have adopted the Bain RAPID framework to help us make high quality decisions quickly and consistently. In addition, we run bi-weekly Business Review Meetings (BRMs) with leaders in the business to drive accountability on key priorities. These meetings also create transparency within the organization and space for healthy collaboration.

You’ve also been a board member at Culture Amp for several years now. What advice would you give to other operators considering their first board seat? 

ROLI: If you are considering a board role, be honest with why you want to be on a board. Being on a board is a time commitment and it is something that you need to evaluate how it fits into your personal and professional commitments. Assuming you have the bandwidth, deeply understand what value you will bring to a board and are able to articulate that effectively. For me my motivation was to leverage my experience in scaling GTM functions to help CEOs and founders that have found product market fit operationalize to scale. Once you have strong value prop, let your network know that you are looking for a board role and you will find opportunities come your way.

When you land your first board position, I would recommend avoiding the first time board member mistake that I hear many of us have made. As a first time board member, you are anxious to show your value and often lean too much into advising the management team on how to run their business. The CEO and the management team are closest to their business and have reasons for their decisions. The best board members ask open ended questions that shine a light on an area the management team isn’t thinking about or challenge their assumptions. Additionally, as a board member your role is not only to have fiduciary responsibility for the company’s operations but also to be their cheerleader. Running a company and operating a business is hard and having partners on your board goes a very long way.

You’ve given excellent advice about guarding your time. Can you summarize some of your best tips for prioritization? 

ROLI: I put boundaries on my calendar and manage them ferociously. I spend time on Sundays writing down the 1-2 things I would like to accomplish that week. Then I make sure I carve time out on my calendar to work on them. Finally, before signing up for a project or priority, I ask myself two questions:

  1. Where does this fit into our business or my personal priorities? If it’s high on the list, why does this activity/project need to happen now?
  2. Am I the best person to do it?

I often find that by the time I am done answering these two questions, my to-do list is much smaller than what I started with.

What’s your secret super power or your biggest kryptonite? 

ROLI: One of my super powers is building authentic relationships quickly, which over time has translated to a large network. I am always happy to help connect people within my network. My kryptonite is not being able to disconnect after work or on weekends. In the short run, it works fine, but if left unchecked it leads to burnout.

What’s one thing you’ve done to empower the next generation of underrepresented leaders?  

ROLI: There are a few things I am proud of — one is leading and building the LinkedIn Women in Leadership Network, along with a few of my colleagues. The program was launched in 2013 and it is great to see the impact it has driven for raising women in leadership roles. The second one is launching a fund (Neythri Futures Fund) with 90%+ of LPs who are women operators from South Asian descent. I find it fascinating how many South Asian men participate in venture as VCs or LPs, compared to very few women. Creating economic opportunity and access for that group has been fun so far.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Syndio: the secret to workplace equity success

The company: Syndio

Syndio is the first people analytics platform that helps companies attain — and sustain — equal pay for equal work. Its real-time software enables rapid, dynamic pay and opportunity gap analysis, without bias. By empowering companies to go from fixing equity issues to proactively monitoring and preventing them, Syndio helps businesses show employees they’re valued. 

Syndio’s origin

The company was founded in 2017 by Zev Eigen, a former law professor who wanted to bring the best technology, lawyers, statisticians, labor economists, and data scientists together to solve hard problems that make the world better. After years of applying machine learning, econometrics, and statistics to help clients audit their pay gaps and other HR risks, he realized he could spark real, lasting changes by automating this complex work for continuous analysis. He brought on Smartsheets co-founder (and mother of seven) Maria Colacurcio as CEO in 2018, and the company’s impact has mushroomed ever since.

Why you should pay attention 

With the social movements of the past few years, pay transparency has become table stakes in larger conversations about workplace equity. Employees want to know that their company values their contributions, but 82% believe their work environment lacks fairness

Many of the world’s leading businesses are finally sitting up and taking notice. Hundreds of companies, such as General Mills, Nordstrom, and Salesforce (and 10% of the Fortune 200) use Syndio to measure the pay of over 2.6 million employees in the United States — proving to their employees, regulators, investors, and themselves that people truly are their most valuable asset. 

The details 

Syndio is the only SaaS platform that not only helps companies find pay disparities based on race, gender, ethnicity, or any other demographic designation, but empowers them to fix those issues and stay in compliance over time. Its suite of tools and services includes a feature that calculates a safe pay range for new hires in order to maintain overall equity, statistical analysis that compares organizations against their peers, and easy-to-understand dashboards and interactive charts to simplify the complexities of workplace equity.

How it works

The Syndio Workplace Equity Platform analyzes a company’s internal HR and compensation data in seconds, compares it to external benchmarks, and makes it easier for companies to understand inequities across pay, promotions, and more. Syndio’s team of expert advisors also provides legal best practices, analytics expertise, and communications guidance.

Syndio helps customers measure and improve all facets of workplace equity — from reducing pay gaps to hiring, promoting, and retaining employees equitably. Unlike a point-in-time analysis, Syndio’s patent-pending PayEQ™ solution provides an always-on-view of pay equity and real-time insights that guide fair pay decisions. And the company’s newest offering, OppEQ™, helps companies measure equity in career development, set realistic diversity goals, and prioritize their greatest areas of opportunity. 

Why were obsessed 

Zev and Maria have built just the right SaaS solution at just the right time. Companies can no longer ignore rising demands to overcome bias, increase diversity, and close gender and racial pay gaps. In order to measure, achieve, and sustain workplace equity, they need objective, data-based recommendations. However, less than a third of HR professionals say their organizations are good at making positive changes based on people analytics data.

With the “great resignation” underway, businesses simply can’t afford to allow biases to fester and increase costly attrition. Truly great companies are looking for solutions like Syndio that help them embed workplace equity into their core and build diverse, dynamic teams to achieve enduring success. That’s fueled the company’s tripling of ARR for the last two years running, and we’re thrilled to support the team in bringing pay equity to even more companies in the years to come.

Get involved

If you want to dig deeper into workplace equity at your own company, request a demo from Syndio and follow @syndioinc.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

OpCo Updates: Taking On 2022

As with any startup journey, the first phase is to prove that the core idea works. Product market fit, if you will. Coming out of 2021, we’ve invested in 42 portfolio companies (21 core, 21 supporting):

  • Six became unicorns and/or unicorns+ and one went public
  • There’s been a $12.7B change in valuation from our initial investment to the latest round
  • Our companies had 23 follow-on rounds, 16 of which were pre-emptions

Thanks to the many talented operators, founders, co-investors and collaborators across our collective, our model is working. Active operators who are building and scaling the world’s most successful companies like Cloudflare, Confluent, Zoom, Salesforce, and Stripe are now engaged in the venture ecosystem to accelerate the success of our values-aligned founders. We are so honored to be on this journey together.

The next stage of any startup? Double down on what works and then scale, starting with the key to it all: the team.


First, we’ve brought on a phenomenal team to channel and further amplify our operator community to help our founders accelerate. Welcome to the new Operator Collective Platform team! We’re so fortunate to have the best of the best leading the charge.

  • Pam Kostka (longtime OpCo LP, former SaaS CEO & All Raise CEO)
  • Caroline Caswell (former VP Marketing All Raise & Pramana Collective)
  • Angie Coleman (former Dir Community, LesbiansWhoTech & Snowflake) 

Operating Partners

Engaging active operators across our community is one of the most impactful value adds we offer. To help that value reach new heights, we created a new part-time Operating Partner role that allows active operators to dedicate time each week to advise our portfolio companies, unlock access to the secret sauce of our collective functional experts, and vet investment opportunities.

Ambrosia Vertesi has transitioned from full-time Operating Partner to part-time, and joined one of our growth stage portfolio companies as Chief People Officer. While many of our companies have been trying to recruit Ambrosia for years, here’s more on why Ironclad was the lucky one that got her and why the timing is now. We are so grateful to Ambrosia for being a key part of OpCo since the very early days, as an LP and then as our first employee three years ago – her impact has been enormous. We’re thrilled she’s staying connected to continue to support our portfolio founders on a more limited basis, and that the virtuous cycle between operating and venture is in motion. 

One of our most highly requested LP intros, Dini Mehta, is also joining us as an Operating Partner, while continuing as Chief Revenue Officer of Lattice. She brings a wealth of energy and expertise on scaling revenue from Series A through growth stage to unicorn+ status. One focus for Operating Partners will be to implement a model that efficiently and effectively engages our functional leaders as cohorts, allowing us to expand our founder support as our portfolio grows. Much more to come about this role and initiatives, upcoming events, and ways to connect in the coming months. 


We’re also delighted to announce Anna Jacobson’s promotion to VP, Operations & Data. She’s been an integral part of the team since joining almost two years ago. Read more about how we met here. And Guergana Tomova, our new part-time CFO brings a wealth of experience with a number of well established venture funds. 

Board of Advisors

We know that companies are successful because of the people who run them. We are honored to add more incredible talent to ours, and, alongside our Board of Advisors (Leyla Seka, Erica Ruliffson Schultz, Claire Hughes Johnson, Stacy Brown-Philpot, Tekedra Mawakana, and Elena Gomez) and longtime Investment Advisory Committee members Dan Scheinman and Magdalena Yesil, we’re ready for the next stage of our own startup journey. We can’t wait to share what’s next.

Operator Collective Board of Advisors
Operator Collective Board of Advisors (from left: Erica Ruliffson Schultz: President of Field Operations, Confluent; Claire Hughes Johnson: Corporate Officer and Former COO, Stripe; Stacy Brown-Philpot: former CEO, TaskRabbit; Leyla Seka: COO, Ironclad; Mallun Yen: Founder & GP, Operator Collective; Tekedra Mawakana: Co-CEO, Waymo; Elena Gomez: CFO, Toast)

1 x 1 = 100: Celebrating 2 Years of Community

Like many start-ups, Operator Collective began as an idea that would not leave my head. Obsessed, I would test the idea with seemingly anyone who would listen–vetting the thesis, seeking out potential supporters as well as naysayers, and unearthing insights. After countless hours, a new collaborative model for venture was born. One that required tearing apart the traditional structure and rebuilding it from the ground up to optimize for a large number of operator investors, most of whom had not invested in venture before. 

Operator Collective was always designed to be a community, not just a fund. It was constructed to bring together values- and incentive-aligned individuals whose networks didn’t naturally intersect. We sought to make venture accessible to the very people tech startups need most but who had been left out: experienced operators from diverse backgrounds who had built and scaled up the most admired companies in the world. By bringing in these highly talented but underrepresented individuals, we believed we could create a multiplier effect. We would change the tech industry from the ground up. 

It turns out that 1×1 can equal 100. This visualization of our connections data proves out that initial hypothesis

Visualization of the Operator Collective network over two years
Each dot represents a person, whether an operator LP or a portfolio company founder. With each individual who was introduced, connections immediately started happening, and our community grew rapidly. Notably, operators helped not only our portfolio companies but each other as well. 

Linking these dots, each line above represents a connection we have made: 

  • an investment opportunity
  • an introduction to a prospective customer or candidate
  • a referral for an open position, board seat, or advisor role
  • a tapped resource for diligence
  • a sharing of expertise or advice, whether about a business issue or professional one

These connections led to so many rewarding and tangible real-world outcomes: companies grew, new customers were signed, hires were made, and new bonds were forged between networks that had previously been separated–leading to yet more connections, and further growth.

Two years after our public launch, I reflect back with immense gratitude. Operator Collective would not be where it is today if not for the early supporters who signed on when this was still just an idea and for the many who’ve generously contributed every step along the way. 

My deepest heartfelt thank you to you, our community of operators, founders, co-investors, advisors, supporters, and of course the phenomenal Operator Collective team for believing in our vision and joining this journey to make the world a better place. Happiest of holidays from all of us at Operator Collective!

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

Operator Spotlight: Tech Leader Li Fan

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke with Li Fan, who has led all kinds of engineering and tech organizations—from Pinterest to Google, Lime, and her newest position as CTO at digital currency platform Circle.

Tell us about your road to tech, and how you overcame any bumps along the way.

Li: I grew up in Shanghai, China, and dreamed of being a designer or architect but my mom pressured me to focus on Science and Engineering (as almost every parent in China did at the time). I didn’t learn real programming until college. I chose the major because my teachers told me that computer science was the “future” and I had enough math skills to master it. My first year in college was a disaster. I just didn’t understand what programming was about. If there was an option to change majors at that time, I’m sure I would have taken that.

Unfortunately (or fortunately) the school didn’t allow it so I had to stick with computer science. The second year, I learned assembly language. Many of my classmates disliked the low-level machine language but I somehow clicked by grinding through one instruction at a time. I had a lightbulb moment during one assignment and after that, programming became natural to me.

How has your experience as a first-generation immigrant influenced the way you think about fostering inclusivity and empathy?

Li: When I started my career 22 years ago, my language skills were barely enough for me to get my professional work done. I lacked the cultural background to make deep connections with non-Chinese co-workers. When they talked about an old movie that they grew up watching, or a joke from a famous talk show, I was clueless. I remember feeling lonely at the lunch table, not able to join the lively conversation.

I also remember how grateful I was when my co-workers purposely slowed down their conversation and explained the context to me, knowing I needed this support. Later, when I was in a leadership position and hosted meetings or dinners, I always noticed those “outsiders” who sat quietly in the corner. I understand how one might feel even if he or she looks fine. I try my best to include them in the conversation, and pay special attention to them to let them know they are part of the family.

How has the ongoing era of remote work changed dynamics amongst tech teams? How has this impacted your approach in starting a new leadership role mid-pandemic?

LI: Before COVID, I was not a big fan of remote work. I value in-person interaction and real-time communication very much. After a few months of working remotely, reality sunk in and I had to adjust my work style in order to manage the team effectively over video calls. By the time I joined Circle, a fully remote crypto company, I was completely converted. I enjoy the extra two hours I save from not commuting to work every day (replaced with regular exercise and cooking time).

Nevertheless, not being in the same physical space still presents challenges. For one, over-communication is definitely a must. People rely more on Slack (for real-time interaction) but such tools are not the best for important notices or decision sharing. Some can feel they are “left out” unintentionally, which impacts their work. I now remind both myself and my team to communicate important messages again and again, both in verbal and written format.

Secondly, people need “hallway chats.” When you meet random co-workers at a break room in the physical world, you share unplanned information (both work or non-work-related). Those small talks build trust and connection. In the virtual world, it is hard to re-create this, so we need to be intentional about making connections. I start smaller meetings by asking about weekend activities or family vacation plans or recent books read, purposely diverting from the main topic in order to build those connections.

Finding world-class tech talent is always a struggle. What can early-stage companies do to build a team that matches the caliber of the Googles of the world?

Li: Early startups don’t have the brand or resources big companies have. It is very hard to compete if the candidates were looking for a brand to put on their resume or a low-risk compensation package. However, there are still plenty of talented people who are willing to take risks and work on new areas. The key to recruiting is to explain the risk/benefit of your company.

Tell a convincing story – You have to have the conviction of the company mission and market story before you can sell this to others. 99% of the candidates I talk to ask me “why did you join this company?” I always take 10-15 minutes to explain the research I did, the motivation I had, and the trade-offs I made before I made my choice. I also go further to explain why they should choose this company (or occasionally, why this might not be a good choice for them).

Understand their motivation – Good talent has options, so I never take their interest for granted. Even for those who worked with me before, I try to understand what’s motivating them to move. Comp is a foundation (so you can’t really under-pay and expect talent to jump for mission alone), but most of the time what gets a candidate over is the scope of work, the growth of the product, or an inspirational manager that they can learn from. The best talent wants to grow, so explain what you can offer (bigger platform, chance to build a team from scratch, working on high risk, high potential project, etc).

Female CTOs are hard to find. What advice do you give to female engineers with leadership aspirations?

LI: I always felt I could do more, have a bigger impact, learn new things, and challenge myself to be better. So I looked for those opportunities and focused on opening up more paths for myself. I have had frustrating moments when I realized that I was not in the “club” and was unfairly judged, but I told myself it would be their loss more than mine. My advice is to focus on what you can control and what is ahead of you. Be confident that you will come back from setbacks, accept the harsh reality but do not be defeated by it. Resilience will prevail

We loved your comments about mentorship in the recent Engineering Leadership podcast. What’s one misstep you’d caution new mentors (or mentees) to watch out for?

LI: When people asked me for career advice, my instinct used to be to immediately jump in and start to analyze the change for this person. Subconsciously I thought that they had similar criteria as I had when choosing career paths. It didn’t take long for me to realize that those assumptions were so wrong. 

Everyone’s life experience is different. What I value most might not be the top concern for others. There is no right or wrong when one makes a life choice, only the one that fits best in a situation. I started asking more questions, like: why do you want to change now, what’s your motivation, what do you want to achieve? If things do not happen as you expected, what would you do? Now my mentoring is more like coaching, leading the path by asking questions instead of giving answers. 

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

LI: Interview more diverse leaders, founders, or board members, and give them an opportunity to shine in front of a bigger audience. I’ve met so many impressive women leaders and I sometimes wonder why they haven’t been discovered yet. In my experience, those diverse talents often work harder and smarter when given the opportunity because they don’t take it for granted.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

LI: My first paying job was at Cisco Systems, where I wrote and ran network simulations and analyzed results of different routing algorithms. I developed a specific idea of the scope of work for a software engineer, but then I joined Ingrian networks, a 10-person startup. I was hired to design high-performance web proxies but I soon found myself having to solve all kinds of issues — from compiler performance, release schedules, integration testing, UI bug fixes, network cable issues, hard disk failures, etc. Everything that our storage appliance touched or relied on, I had to understand and be ready to jump in because we were a small team. 

I soon understood that the “job description” doesn’t matter when it comes to getting results. You do what needs to be done. I learned to be adaptive and flexible at Ingrian. I played any role required, data analyst, testing engineer, UI designer, release engineer, or even receptionist or sales rep. I learned to pick up new skills on the job quickly and not be afraid of unknowns. This became one of my strengths that pushed me ahead in my later career.

What’s your secret super power? 

Li: I’m relatable to many people. I love technology and art. I’m a mom of two who volunteers in school while working full time at a FinTech company as an executive. I love spending time with my friends at happy hour or weekend hiking. I grew up in China but have spent half of my life in the US. These diverse life experiences give me the ability to understand and connect with many wonderful people, and learn from their wisdom and insight.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Meet Voiceflow: The force that’s democratizing conversational AI

The company: Voiceflow

Voiceflow is a visual design tool for conversational AI teams. It helps them design, prototype, and launch conversational interfaces across just about any channel—everything from those interactive voice response (IVR) phone systems we all know and (rarely) love, to web, chat, voice assistants, in-car, mobile apps, drive-thrus, and more.

Why you should pay attention 

With the prevalence of Amazon’s Alexa, Apple’s Siri, and all the rest, conversational AI is everywhere. It now powers trillions of conversations every year for things like customer support, simple transactions, and information gathering. All types of companies—not just tech giants—are investing in a new generation of conversation designers to help them meet user expectations, reduce costs, and extend their brand persona with innovative, flexible experiences.

In fact, the voice assistant application market is projected to grow to $11.2 billion by 2026 while the global conversational AI market size should reach $18.4 billion in that same time. However, traditional tools in this space were developed for designing automated call flows in 90s-era call centers. Their overly complex approaches simply didn’t cut it once COVID sent every consumer brand scrambling to reinvent and launch new digital experiences last year.

The details 

Voiceflow recognized this problem early on and created a modern creative platform in 2019 to help conversational AI teams work together, design great conversations, and iterate quickly. This year, over 80,000 designers, developers, and teams—at businesses like McDonald’s, Google, Spotify, Ford, Motorola, Amazon, BMW, and US Bank—generated more than 550 million conversational interactions using Voiceflow. It’s helping unify their design and prototyping workflows so they can easily launch banking assistants, IVR experiences, entertainment applications, games, support bots, and other live experiences for end users.

How it works

Voiceflow empowers teams to design, prototype, and launch chat and voice bots across channels like IVR, messenger, Alexa, Google Assistant, and web chat. Conversational AI designers can use Voiceflow’s intuitive, drag-and-drop visual editor to connect steps and blocks together and create sophisticated conversation designs in minutes. The system also provides shared team workspaces, auto-syncing and versioning, reusable components and templates, and omni-channel management tools.

Screenshot of in-car assistant conversational AI flow

This gives people at every level of technical expertise a visual way to build, test, and manage great conversations. Some customers also leverage Voiceflow’s open source API to support their full design-to-development pipeline for launching and actually hosting conversation experiences across any channel.

Why we’re obsessed

Voiceflow is on a mission to democratize conversational AI by creating a modern collaboration platform for these interfaces. And it’s working. The market is growing exponentially and more people are dedicating their careers to the space (Voiceflow’s user base grew by 60% this year alone). Conversation designers love having Voiceflow in their tech stack because it is legitimizing the tactics, methodologies, and industry standards for conversation design.

Customers like Home Depot have touted amazing results, such as scaling user testing from 12 tests to 300 in one week. In addition, Voiceflow has cultivated an active global community of 8,000 (and growing) conversation designers who now have a forum where they can connect with each other, up-level their skills, swap best practices, or recruit top talent in this emerging discipline.

Voiceflow’s origin

Company founders Braden Ream, Andrew Lawrence, Michael Hood, and Tyler Han joined forces back in 2018 to create a fun choose-your-own-adventure children’s stories app for Alexa, but quickly pivoted when they realized how difficult it was to collaborate in the world of nonlinear conversations. Their timing couldn’t have been better, since the pandemic brought these types of high ROI, socially distanced customer experiences to the top of every CTO’s priority list. And as the company has scaled rapidly to meet this demand, its founders are building a diverse, global team with a culture of creativity, curiosity, and owners.

Get involved

If you have a conversational AI team that could benefit from easier collaboration, be sure to have them check out Voiceflow to start building for free.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

The ins & outs of SaaS metrics: Finance leader Christina Ross on revenue retention

With all the acronyms being thrown about, you may be left wondering which SaaS metrics are the best indicators of performance? Which ones do investors focus on? Christina Ross, CFO turned CEO/co-founder of Cube, not only analyzes these metrics for her own business, but brings decades of finance experience to the task of automating and optimizing strategic financial planning and analysis for other companies. 

In this blog series, we’ll hear firsthand from Christina about how to calculate and interpret the most helpful measurements of enterprise software success. To start off, we asked her about two metrics that help businesses measure customer retention and growth: gross revenue retention and net revenue retention.

At a high level, what is revenue retention and why does it matter?

CHRISTINA: Revenue retention is a measure of how much revenue a business keeps from the same customer base over a certain time period. You can track it by month, quarter, year, week, or even day. 

One important note is that revenue retention only refers to existing customers. Acquiring a new customer—and the associated revenue they bring in—can be 5 to 25 times more expensive than retaining one (in terms of time, resources, and finances). Thus, revenue retention is a good measure of sustainability and profitability. Customers with reliable revenue retention have a stable runway and are more profitable in the long run.

Can you get the same insights by tracking customer or logo retention?

CHRISTINA: Not all customers are created equal. One customer might constitute 30% of a company’s revenue while another just makes up 0.05%. Losing any customer hurts, but those that represent a greater share of revenue will hurt a lot more. Tracking revenue retention alongside customer retention can help you get the full picture, especially when you look at both gross revenue retention (GRR) and net revenue retention (NRR). 

What exactly is gross revenue retention (GRR) and why is it important to track? 

CHRISTINA: Gross revenue retention is the percentage of revenue a business retained from the start of a specific period. It shows how successful you’ve been in retaining customers at current price points or contract values.

GRR = (MRR – Churn – Contractions) / MRR

MRR is your monthly recurring revenue at the start of the month, churn is the amount lost (in dollars) to customers who are no longer customers, and contractions is the amount lost from customers who downgraded to a less expensive plan. Even if you earn new sales or upgrade revenue in a given month, this formula looks only at revenue retention as opposed to acquisition. The closer GRR is to 100%, the better. That said, this depends on your customers’ size, since higher churn is often expected from SMBs. 

If GRR is low, it could signal a few problems with your business’ health. For example, you might not be solving the right problem. People won’t stick around if the problem you’re solving is too small to warrant your price for the solution. Other issues might be that your customer experience is frustrating, or your customers simply don’t use the product enough. If people only log in once a month, you’re not building trust or loyalty with them.

How is net revenue retention (NRR) different?

CHRISTINA: GRR doesn’t account for new customers or expansions. It only looks at what you started with and how much you’ve lost, while net revenue retention (also known as “net dollar retention” or NDR) is the total change in recurring revenue. It tracks both your business’ ability to retain and acquire revenue from existing customers.  

NRR = (MRR + Expansions – Churn – Contractions) / MRR

As you can see, what’s different here is that we’re accounting for expansions, or the new money a group of customers have spent with your business. Even though NRR is a growth indicator, it’s still a retention metric, so we don’t include new sales. NRR measures how well a business’ cross-sell and upsell strategies are working.

Experts say a good median NRR for private companies is 104%, and generally NRR > 100% indicates growth, while NRR < 100% indicates decline. Businesses with high NRR are offering the right things customers need as they grow. On the other hand, when NRR is consistently low, this should sound alarm bells. It could mean the company isn’t offering the right upgrades to incentivize customers to move up the value ladder. Maybe the customer success experience is frustrating, or there’s not enough brand loyalty to prevent switching.

What does the combination of GRR and NRR tell us?

CHRISTINA: The best insights come from cross-referencing NRR and GRR. SaaS companies that have both high GRR and high NRR are in a great place and can focus on acquiring new customers. But if you have high GRR and low NRR, it means you’re good at keeping customers, but need to get better at selling to them again, perhaps by rethinking the upgrades you’re offering. And if you have both low NRR and low GRR, there are likely some larger underlying issues that need to be addressed quickly. This might require you to radically invest in customer support or take a hard look at the problem you’re trying to solve.

If there’s a problem with GRR or NRR, how can we improve these metrics?

CHRISTINA: At the end of the day, people are the ones who make the decision to churn or not. So while we might calculate revenue retention metrics separately from customer churn, in practical terms, there’s no separating them. When it comes to increasing GRR, the best strategies focus on keeping your customers involved and happy—improving the overall customer experience, building trust, or adding more integrations. 

Much of this will indirectly improve NRR as well, because it reduces churn and contractions. If you want to double down on NRR, focus on expansions—improving customer service, refining your value ladder, or adopting a customer expansion strategy. All of this can be informed by cohort analysis, which might help you hone in on what you need to do to better support the specific customer groups that are responsible for the majority of your churn.

Of course, don’t forget that these revenue metrics only look at existing customers, so it’s best to combine them with other KPIs for a full picture of what’s happening in the business. GRR doesn’t account for any growth and NRR may obscure and cloak a churn problem. To learn more about these and other important SaaS metrics, check out our recent blog post on GRR and NRR.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

Why we’re amped about Amplitude

There was a time it felt like everywhere we turned, someone was telling us to take a look at Amplitude. This was coming not only from our network of Operator LPs at larger enterprises, but also startup founders in our portfolio. Folks were raving both about how Amplitude’s analytics platform provides step-by-step data on the performance of a digital product, as well as how particularly thoughtful and values-driven the Amplitude founders are. When we met co-founder and CEO Spenser Skates, we knew we wanted to be a part of Amplitude’s journey.

The company: Amplitude

Amplitude is the first unified product analytics system that brings together an entirely new depth of customer understanding with the speed of action needed to optimize experiences in the moment. A pioneer in digital optimization, its software enables organizations to see and predict which combination of features and actions translate to business outcomes — and then intelligently adapt each digital experience based on these insights.

Why you should pay attention 

In a pandemic world, companies no longer have much of a choice about whether to invest in digital transformation — they need amazing digital products in order to survive. Even before COVID-19, analysts were predicting that companies would deploy over 500 million digital apps by 2023. They’re now expecting 65% of the global economy to be digitized by next year. And the next frontier of digital transformation is digital optimization.

Although the revenue center for most companies is shifting from sales and marketing to product, many of the teams building these products still rely on their intuition to analyze performance. That approach just doesn’t cut it anymore. In order to keep up with the pace of disruption in our more digital-than-ever landscape, product teams require a fundamentally new approach. They need 360-degree insight into the entire digital experience. Only then can they make data-driven bets that transform customer value. Enter Amplitude’s digital optimization system.

The details 

Amplitude has changed the game for more than 1,200 organizations, including B2B software companies such as Atlassian, Intuit, and Hubspot, as well as consumer brands like Twitter, Walmart, Instacart, and Spirit Airlines (along with 26 of the Fortune 100). Its digital optimization system is the “Moneyball” brains behind 45,000+ digital products. Amplitude’s software helps these teams innovate faster and smarter by giving them fine-grained performance data that goes way deeper than the basic ad clicks and page views of previous decades. 

It shows them exactly how specific combinations of features and user actions translate to customer retention, loyalty, lifetime value, and other business outcomes. With this data, they can make strategic decisions — like whether to launch a big feature or change a distribution channel. They can experiment, see what’s working and what isn’t, and make changes to their product based on real-time behavior.

How it works

Amplitude’s platform tracks 900 billion customer behaviors each month in a privacy-conscious way. It aggregates all this data and uses machine learning to segment users, predict outcomes, and uncover relevant patterns throughout the digital journey. For example, Amplitude’s product analytics help teams find ways to quickly reduce friction and double-down on features that increase revenue. Earlier this year, the company also launched new solutions to help product and marketing teams easily personalize digital touchpoints and test experiences with key segments.

All of these solutions are powered by Amplitude’s proprietary behavioral graph, which was invented by company founder and chief architect, Jeffrey Wang. Built for the complexity of modern digital products, its native query engine and machine learning algorithms correlate every individual action taken across a digital product to understand and predict which behaviors are indicators of certain outcomes. 

Amplitude’s origin

Amplitude was founded in 2012 by former MIT alums (and Battlecode competition opponents) Curtis Liu and Spenser Skates, along with Stanford grad Jeffrey Wang. Curtis and Spenser had actually taken a stab at another startup (a voice recognition app called Sonalight) before that but decided it was a little too early for its time. However, they realized the product analytics tool they had built to better understand how customers were using Sonalight could actually be more valuable. Clearly, they were right about that, and Amplitude has been a rocketship ever since, culminating in a successful direct listing last month. 

Get involved

To find out more about Amplitude’s digital optimization system, explore its product demo or customer stories. And while you’re there, it’s worth a look at the company’s many career opportunities

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

Operator Spotlight: Finance Leader Elena Gomez

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke with Elena Gomez, CFO at Toast and the newest member of Operator Collective’s Board of Advisors.

Congratulations on Toast’s IPO last month. Tell us about the company, and what it was like to join at such a pivotal time for the business.

ELENA: I’m super excited to have joined Toast earlier this year and helped shepherd them through an IPO process. But in reality, the IPO is just a stop on our journey. I’m even more excited for what’s to come for Toast. We have big ambitions to continue to grow and power restaurants of all sizes on our platform. 

For those of you not familiar with the company: Toast is a cloud-based, end-to-end platform that is purpose-built for the restaurant industry. We have almost 50,000 restaurants on our platform. Restaurants are complex businesses with a lot of moving parts. And by working with them and understanding their needs, we’ve built a comprehensive suite of subscription services, hardware, and financial technology solutions. We aim to help restaurants of all sizes streamline nearly every aspect of their operation. 

You’ve worked for wildly successful public companies like Zendesk and Salesforce. What are some key practices or learnings that you took forward into your new CFO role at Toast?

ELENA: There are several learnings but I’ll boil it down to three: 

  1. Putting the customer at the center of what we do. Customer success is a key principle at Toast. Similar to Zendesk and Salesforce, we put the customer at the center of all of our decisions. We want to help restaurants in our communities thrive especially after the tough last 18 months of Covid. I personally look forward to meeting customers and understanding how we can make their businesses more successful. 
  2. Building a world-class organization with an eye towards diversity. It’s a hot market and we are living in an unprecedented time. But nonetheless, we have big ambitions at Toast to continue to grow as restaurants come out of the pandemic stronger than before. To achieve our goals, we will continue to add employees to the Toast family. Hiring diverse talent is a key part of the playbook at Zendesk and Salesforce, and it has been a game-changer. One of the reasons I joined Toast was because they value diversity as well. This week I joined a fireside panel with our Latinx employee resource group, “Migente”. I was excited to see over 100 Latinx Toasters participating on the call.  
  3. Staying agile and scrappy. If there is anything I learned at Zendesk and Salesforce it is to stay agile and scrappy. Even the best of plans can have a curveball thrown in the mix. For many of us, Covid was a major curveball. Customer expectations will continue to go up and evolve, so staying agile/flexible/current on all fronts is very important. The great news is the team at Toast is battlefield-tested. They’ve survived through Covid and given back to restaurants during this time.

What do you advise early-stage companies with IPO aspirations to be thinking about at each point in their trajectory? Any tips to help support financial IPO readiness?  

ELENA: Look for talent with public company experience, especially in finance and legal. Don’t wait too long to hire your CFO, VP of Finance, and Controller. Oftentimes, founders hire one leader to figure out the accounting side and expect that same person to do the finance side. I believe you need both or you will never get the headlights out further because the finance leader will be stuck closing the books. 

In terms of financial IPO readiness, I would make sure you deeply understand the path to sustainable growth. This means knowing the metrics and assumptions of what will drive durable growth, and ensuring the critical exec team is bought off on them. Next, I would understand some of the basic hygiene things in finance — how well the team closes the books, how they do their forecasting process, etc. And of course, pick your board carefully. Find a balance of operators and ex-operators. 

You’ve led finance in SaaS businesses for more than a decade. Which company-level metrics do you tend to monitor most closely? 

ELENA: Love this question. First and foremost, I look for growth across the board. But metrics I pay a lot of attention to are: ARR Growth, Net Retention and Churn rates, CAC, and Payback periods. If you can drive healthy NRR with solid unit economics, you will continue to sustain durable growth over time. 

You are a board member at PagerDuty and Smartsheet as the audit committee chair. How do you measure your success in that role? And what advice would you have for someone in that position for the first time? 

ELENA: I focus on making sure I continue to add value for Jen and Mark and to their management teams. In order to do that, I stay current on key themes, read all the board materials, and often connect with other board members or management in between board meetings to get a pulse of key issues or themes emerging. As a board member, you will be exposed to many different topics, and there will be great quarters as well as tougher quarters. Being a steady sounding board through all of it is important. 

But even more important, is to not be afraid to offer constructive feedback. Most CEOs want a board that is willing to lean in and offer a balanced outsider perspective. As a new board member, I would encourage you to build a relationship with another board member outside the boardroom. Over time, the relationships will build naturally but I found it super beneficial to have a board member I could call when I didn’t understand something and/or someone I could debate a specific topic with outside the board room. 

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

ELENA: Well, I have to say this is so so hard. We have a pipeline problem. I would love to see venture and tech firms partner with local universities and colleges to change the diversity of graduating students. Even the best of companies — that are looking for diverse talent and have great intentions — don’t have the pipeline to succeed. 

In addition to fixing the pipeline problem, we can initiate change in the workplace as well. Some ideas that come to mind are focusing on funding startups with diverse founders, coupled with placing diverse talent across tech (startups and large tech). One of the reasons I joined Operator Collective was because I admire the ambition of changing how venture is done. Operator Collective is just one example of how we can begin to make the change we need to see.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

ELENA: One job I had was helping my mom with her AVON sales. She sold AVON to her family and friends so we could have extra money. I helped her write out the orders, deliver the catalogs, and sort the purchases when they arrived. Technically it wasn’t a paid job, but my mom loved the help. I learned to organize my tasks but also observed my mom juggle two jobs. That work ethic has passed on to me now. 

Another job I had was working at Longs Drugs (now CVS). I was a checker and occasionally worked the inventory on the floor. Sounds silly, but at 16 I knew that inventory on the shelves had to be found easily by customers or they wouldn’t buy it. Kind of reminds me of conversations I have now around taking friction out of the buying process. I enjoyed being friendly to my customers and checking them out quickly, and learned the most basic customer success skills. All of my happy customers kept coming back! 

What’s your secret super power? 

ELENA: I can connect the dots and have fairly decent emotional EQ. This has helped me tremendously in my career. As a leader, connecting people and insights across an organization just makes your job easier. In addition, understanding people’s emotions can help you resolve issues faster, connect with a customer or employee, and have greater empathy for them.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Supercharge sales productivity with an all-in-one “Scratchpad”

Meet Scratchpad, the digital workspace that puts an intuitive interface on top of Salesforce

The company: Scratchpad

Nearly all account executives use Salesforce, but most of their work is done in other places such as spreadsheets, note-taking apps, task managers, and calendars. This leaves data spread across tools and apps that never finds its way back to the organization. Scratchpad is the first workspace built for sales to solve this problem. It combines everything a rep needs for their daily work in a single intuitive interface. In less than 30 seconds, revenue teams can set up Scratchpad and start improving their data flows and forecasts to consistently attain quotas. 

Why you should pay attention 

While Salesforce is a powerful database, it doesn’t make it easy for day-to-day users to stay organized, manage meetings, update and share sales notes, follow through on next steps, set tasks, or collaborate. Instead, many AEs hack together general-purpose tools that usually remain completely siloed from each other and the system of record.  

With dozens or hundreds of tasks each day, every click matters. On average, sales professionals spend only about a third of their time selling. By eliminating duplicative data entry, Scratchpad helps AEs spend more time doing what they do best: selling. And because it’s seamlessly connected to everything they need in Salesforce, Scratchpad transforms CRM from tedious to delightful.  

The details 

Scratchpad empowers sales reps to do their best work by reducing the number of hoops they have to jump through to get their work done. With this modern workspace, AEs, account managers, and sales engineers at great companies like Algolia, Autodesk, Lacework, Productboard, Segment, Snowflake, Splunk, and Twilio are reducing drag in their sales organizations and helping more reps attain or surpass their quotas.

Scratchpad’s founders recognized early on that CRM was at the center of most revenue teams and always would be, so they thoughtfully designed every feature and interaction with front-line reps in mind. The solution is all about bringing Salesforce to where AEs need to be (whether in their calendar, email, anywhere on the web, or other sales tools) in ways that fit their existing workflows and help increase adoption of the CRM system.

How it works

Scratchpad brings a salesperson’s notes, tasks, customer context (including emails, calendar events, and activity history), spreadsheets, Kanban boards, search, and collaboration tools into one simple view. With this suite of tools, reps have everything they need to manage their day just one click away, so they’re no longer bouncing back and forth from a calendar, to a note-taking app, to tasks, and then to Salesforce. 

Users can quickly and easily update important fields for each opportunity, link their notes, create tasks or contacts, and view contextual data from Salesforce — all from Scratchpad tools embedded into their existing apps. For instance, with the product’s most recent update, they can launch Salesforce data directly from a calendar event view so they always have the full picture they need in order to take action. 

Why were obsessed 

We’re crazy about Scratchpad because the team recognizes that sales is a craft and reps are people like everyone else. Rather than painstakingly updating records, their time should be spent on moving deals forward, building customer relationships, and quality family time! Scratchpad is turning the notion of “boring” enterprise B2B tools on its head and bringing joy and delight into what can be an emotionally taxing job. This means sales managers get better visibility into pipeline health so they’re more efficient with coaching, and revenue operations leads no longer have to rely on best guesses for forecasting. 

Scratchpad’s origin

Serial entrepreneurs Pouyan Salehi and Cyrus Karbassiyoon co-founded Scratchpad in 2019 after observing the challenges salespeople were experiencing in their day-to-day workflows. The pair had previously co-founded another sales technology company, PersistIQ, where they developed a deep understanding and appreciation for the work of a salesperson and the challenges of working within a sales organization. 

Get involved

If you’re interested in learning more about Scratchpad, install its Chrome plugin or sign up for the web app in less than a minute, listen to the team’s Beyond Quota podcast, or check out the company’s many job openings.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.