How to Build a Customer-Centric Org

The show must go on – except when it mustn’t. We loved our Challenge Series webinars, but when the recent social justice movement began, we chose to honor and prioritize our emotions and cancel our final session on Customer Success. It was the right decision, though we also missed hearing great advice from two experienced leaders. Since we couldn’t meet live, we asked our scheduled guests – Gainsight CEO Nick Mehta and Slack VP of Customer Success Christina Kosmowski – if they’d answer our questions anyway, and of course they were happy to do so. We hope you find their advice on building a customer-centric org as helpful as we did. 

What is customer success and how is it different from customer support? 

CHRISTINA: Customer Success (CS) is maximizing business value through the use of your product while ensuring a positive experience. It is proactive and business-value driven. Customer support, on the other hand, is more reactive – responding to a specific issue the customer or user is having. 

NICK: In business models where customers have power (such as SaaS), vendors are accountable not just for the sale or product, but also for the outcome. Customer Success is about getting customers proactively to their desired outcomes with a strong customer experience (CX). In our geeky Gainsight language, we say CS = CO + CX. Customer Support, by nature, is about responding when customers have issues – but what if they never call you and just silently disengage? Customer Success is about owning the outcome.

Nick, people often credit Gainsight with helping to create the customer success industry. Can you tell us a bit what that means and how that played out?

NICK: We definitely didn’t create the industry or category, but perhaps we were the chief cheerleader. We saw a tiny profession in 2013 when we launched Gainsight and knew every business would need CS over time. As such, we launched a conference (Pulse) all about Customer Success best practices and community. We hosted local meetups, online events, executive events, job boards, and more, and we just released our third book. It’s been a lot of heavy lifting, but so rewarding to see how CS has become a must for tech companies now.

Christina, I watched you create an amazing customer success org at Salesforce, and now you’ve done it again at Slack. What are the 3 things everyone needs to know when building a CS team?

CHRISTINA: I love Customer Success. It’s the perfect bridge between technology and business/humans and I’m fortunate to have found two amazingly customer-centric companies. Three things everyone should know: 1) Create a culture of innovation and agility. There’s no template for customer success. It iterates based on where customers are on the journey with your product. Recognize that and build that iteration and culture into your culture. 2) Create a culture of Customer Centricity within your company. Don’t limit it to just the Customer Success team; everyone in every department needs to feel responsible for Customer Success. And 3) Connect your customers. Your customers learn the most from each other, so don’t be afraid to connect them.

Nick, what’s the best way to think about how to create a customer-centric culture if you’re just starting out?  

NICK: Three core steps: First, make sure the leadership team is meeting LOTS of customers; I meet 500+ clients a year and build it into the rhythm of my work, from advisory boards to sales calls to executive business reviews. Second, integrate customer voices into every company event from All Hands to board meetings to internal comms. And third, encourage every employee to hear first-person customer stories – by joining EBRs, inviting customers in to speak, and more.

Christina, Slack has grown like gangbusters during the pandemic (and before). How have you been able to stay close to your customers? 

CHRISTINA: It’s important that we adapt to what’s most important to our customers. Slack is not a work-from-home product, per se, but it definitely helps keep employees connected. As we shifted to remote work, many of our customers were looking to us for advice, so we shifted some of our content and resources to support that. We utilized our connect product (formerly shared channels) to push content in a more dynamic way. And we accelerated launches to get them connected and update features as soon as possible. 

What’s the secret to maintaining a world-class customer success organization as you grow?

CHRISTINA: Keep an open, innovative mind. As your product and customers evolve and their usage with your product evolves, you need to evolve as well. Build processes that consistently bring the customer voice and feedback to your company and hold all the departments accountable to it. And connect with other CS leaders – Nick and Gainsight do an amazing job of connecting us all, and I find that network invaluable. I’m constantly learning from folks, and often the smaller CS organizations bring innovative ideas and remind me that anything is possible. 

NICK: There’s no one recipe and CS varies a lot based upon the complexity of your product and the average deal size for your business. If I had to give 3 tips: 1) have a Beginner’s Mind – read books, listen to podcasts, and attend conferences, 2) Build a peer network for coaching, and 3) Use an agile approach with your team where you change in sprints (every 2 weeks, for example). 

Attrition is a critical metric for customer success teams. What other metrics are critical to become a customer-centric company?

NICK: The other core lagging indicators are expansion and advocacy, but you need to identify leading indicators to manage toward. These could include product usage, sentiment, and other factors. We recommend bubbling these up into an overall north star leading indicator, or a health score. Our standard recommendation is to consider four core elements: Deployment, Engagement, Adoption, and ROI.

CHRISTINA: Yes, I agree – Attrition is an important lagging indicator, but we try to identify health and value earlier in the process so attrition becomes a nonevent. It’s important to measure business value up front and consistently measure. We do that through quarterly business reviews. We also measure health on three components: 1) Qualitative principles we’ve found in successful implementations such as executive sponsorship and training, 2) Quantitative usage metrics, and 3) Engagement with Slack – things like attending events, meetings, and more. 

How have metrics changed since COVID-19? What new metrics are you tracking or paying more attention to?

CHRISTINA: I think COVID-19 is just accelerating and putting more emphasis on achieving business value. We’re maniacally focused on ensuring our customers are getting value and looking at ways to accelerate our launches and activities. 

NICK: I spoke to our advisory board a few weeks ago and asked what they’re doing differently given COVID-19. In general, the theme was they were doing “everything we should have been doing all the time, just more and faster.” I think the biggest new metric is trying to understand the business health of your customers. This ties to also tracking the payment health of your clients in terms of their ability to financially survive.

How do you foster empathy for your customers across the organization? Do you have any programs or tricks you use?

CHRISTINA: Always use data and the customer lens. Tell the story in terms of the customer point of view and how they are experiencing it. 

NICK: A big trick I use is to change language anytime it’s not customer-centric. As a leader, if you hear “the customer is being unreasonable,” challenge it by asking: “Or is the customer just under a lot of stress?” Another example: “The client is so high maintenance” might become “The client is getting us to improve.” Or switch “This client is so frustrating” to something like “I can empathize with what they’re going through right now.”

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


Operator Spotlight: Data and Analytics Leader Anita Lynch

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 to Anita Lynch, Vice President of Data Governance for Disney+ at the Walt Disney Company.

Given the turmoil from both COVID-19 and the recent racial injustices, what are some things companies and teams should prioritize right now? 

ANITA: I can’t speak to what everyone should do, but what I’m doing is carving out more time to listen and reflect. By pulling out of the day-to-day fray and asking bigger picture questions to understand diverse perspectives, it becomes easier for me to identify a faulty assumption or consider the less obvious opportunities as they arise. Recently a friend asked for my advice on how she could engage with her team around these emotionally charged events. The advice I gave is this: This is an opportunity for catharsis with the hope of healing. 

Sharing is best facilitated within an established culture of trust with small group discussions of 10 people or fewer. Even among people we know, we cannot guess what any one person might be struggling with as a related trauma. Create a safe space for discussion by acknowledging the trauma of these events and the fact not everyone knows what to do. Ask people if they’re willing to share – and if so, ask “How is this affecting you?” and “How can we support you?” 

The pandemic and downturn have renewed fears over privacy and data security. What advice do you have for companies looking to navigate those concerns? 

ANITA: COVID-19 has made everyone in the data sector much more aware of the importance of data privacy, user data protection, data quality, and cost optimization. It’s critical to ensure there’s a partnership at the leadership and operational levels between Information Security, Data / Data Engineering, Marketing, Product, and Legal teams. In my organization, the Governance team role sits at the intersection to do this work. 

How has your team at Disney had to change because of COVID-19? 

ANITA: Disney has a strong culture of developing leadership. Today our leaders are spending even more time on coaching, development, and gathering input from our team members who work directly with customers, internal or external. We’re working hard to ensure every unique situation is checked for opportunities to give support and encouragement.

We’re also more focused than ever on transparent communication and delivering high quality work. Repeating iterations of individual work balanced with group work allows us to detect misalignment and share knowledge. Although there’s an element of fatigue resulting from the increased screen time, there’s huge benefit to having broader participation in our quality checks. 

My own team has changed how we collaborate and manage our time, too. We’re geographically distributed, which requires flexibility in scheduling, and we’re more conscious of participation in meetings and discussions. For those technical roles and non-managers, we encourage one day mid-week where they can minimize scheduled meetings to work uninterrupted. 

Are there additional steps smaller and younger companies should take now to prepare for both additional cyber threats and a new reliance on analytics? 

ANITA: Independent of size and stage, companies should have an advisor on data protection and data privacy compliance, in addition to data strategy. The landscape is evolving quickly and smaller companies need to allocate all of their internal focus on building a great product.

Any advice you’d offer someone looking to build a career in analytics?

ANITA: This space is continually evolving, so don’t be tempted to specialize too early. Understanding how data and insights drive value for all the various business functions is the key to eventually becoming an effective leader in the space. Keep challenging yourself to learn new skills and applying them in new contexts.

What’s one amazing insight no one knows about data privacy?   

ANITA: Having a vision for privacy compliance at the outset when architecting a data tech stack for product or marketing analytics is now a competitive advantage. 

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

ANITA: I spent one summer in high school working as a cashier at a Mrs. Field’s Cookies. It was a crash course in general management. I learned how to do math quickly in my head, as well as the importance of managing inventory and supply chain to improve your P&L. I also learned how to build brand awareness – The smell of freshly baked chocolate chip cookies at the right time of day could make all the difference, plus it makes people smile. 

What’s one unconventional thing you’re doing to keep yourself sane these days?

ANITA: I’m paying a lot more attention to my inner dialogue. Before COVID-19, it was common for me to be a bit more critical of myself than perhaps I am with my team or my family. Now I’m actively working on being as empathetic with myself as I’d be with my best friend. Everyone experiences and manages their stress differently, and recognizing when I’m fatigued or stressed is important.

What’s the one spice or condiment you could never live without? 

ANITA: Everything bagel seasoning – for my eggs in the morning!

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

6 words to help you act against racial injustice

I’m a thinker, by nature – someone who’s calm in crisis. When something happens, I process and think; then I take action. Even so – and after much thinking – there are no words to convey how difficult the recent turmoil has been. I’ve started and stopped myself several times from blasting on social media the despair and frustration I feel as a black person in America. Still, I listened to my inner voice and took the time to think about measurable actions that can personally change the lives of those who need our support.

Thank you to everyone who’s reached out – What can we do? Who needs help? How can we act against each injustice? Here is my answer. What it boils down to for me is six simple words: Don’t wait, be intentional, give forward.


In the tech world, it’s easy to throw yourself into life as it happens, leaving little room for passion projects or anything outside the must-do category. We often just go with that flow, but is that how we want to live our lives? I didn’t want to wait to retire to have an impact. Even before I became an executive, I was always happy to help others along my journey and send that figurative elevator back down. The great Maya Angelou once said, “A legacy is not some big grand thing. A legacy is every life you touch.” Simply put: It’s what you do everyday that matters. 

Your legacy is every stand you take and the sooner you start, the more you achieve. Reach out to those Black founders, or take their calls. Offer feedback and make connections. Talk to your Black colleagues, diversify your networks, make the hire, write the check. Don’t wait until “someday” to take action and be the change. Every call you make, every note you send, and every expression of support means more to us than you realize. 

I hope my legacy will be that I made meaningful contributions to the technology and venture capital worlds, while bringing as many people as possible along with me on this journey. What will your legacy be? 


In a recent conversation with Squawk Box, Ariel Investments CEO Mellody Hobson said, “I love the saying: ‘Math has no opinion.’ None. Just count.” Why? Because counting, she points out, will prove that “at all levels of corporate America, people of color black and brown Americans, underrepresented minorities do not show up in the numbers in which we exist in this country.” To fight this, Hobson suggests companies hold themselves accountable by setting targets, just as we set targets and track metrics in so many parts of an organization. 

As a numbers-oriented business leader, this idea really resonated with me. I’ve consistently made John Doerr’s Measure What Matters a requirement for my leadership teams. If you want to achieve audacious goals through OKRs, you must align everyone to maximize those results. Setting OKRs is strategic planning at its core, a powerful tool for prioritization, even when it comes to diversity.

In fact, that purpose and intention is one of the things I love about Operator Collective; partners Mallun Yen and Leyla Seka were deliberate about the LP base they wanted to create. They reached out with purpose, asking several LPs to open their networks so they could build the kind of fund that matched the image they had in their minds. I and others extended our networks to them, and they embraced it. Organizations everywhere would be wise to emulate this intentional diversity. 


A more tangible way to make a difference is to give forward: volunteer your services or donate to reputable organizations doing ground-level work to move the needle on racial equality. But the movement is huge where do you start? Before you offer your time or reach for your wallet, let your interests guide you and consider which organizations will have long-term, forward-looking impact. Core to my personal values are entrepreneurship and education, so I always look to aid organizations that support passionate founders and fight educational inequity. 

I never set out to be an angel investor, but I saw the dearth of support for women and minority founders; plus I’m always looking for those customer problems that can be solved while building a durable competitive advantage. That led to my first pre-seed investment (which was actually more of an investment in founder Morgan DeBaun and her vision). It’s powerful to see your dollars helping someone else; since then I’ve been fortunate to have so many chances to champion small businesses and those who dare to dream, both as an executive at Intuit and as a director on a public bank board. Spreading good is addictive.

According to the Kauffman Foundation research project in partnership with Marlon Nichols, more than 75% of venture rounds raised go to all-White founding teams. As you invest in, mentor, or advise, if you see an all-White team, speak up. Be an ally. Make a connection. This is another simple way to give forward and build the future you want to see now. Silence is implicit acceptance of the status quo. 

In the spirit of transparency in our forward-giving, I’m proud to share a few measures our Operator Collective community has taken as a starting point. We are: 

  • Supporting Black and LatinX founders affected by COVID19. Last month, we joined Paladin’s Project Lifeline as a founding member. COVID-19 has had a disproportionate impact on underrepresented founders and small business owners. Project Lifeline will offer equity-free cash grants, a 4-week accelerator program, and an investor showcase for Black and Latinx startups founders affected. Paladin was founded in 2018 by LP Terell Sterling. Please click here if you’d like to make a donation. 
  • Funding education for Black and LatinX founders. We’re sponsoring a scholarship program for 50 Black and Latinx founders to attend Arlan Hamilton’s intensive course on How to Raise Capital for Your Company from Scratch. If you’re a Black or Latinx founder and would like to apply, please email us at 

  • Empowering the next generation. We’re giving our time and dollars to SMASH, a rigorous five-week residential STEM education program for Black, Latinx, and Native American high school students. Founded in 2004 by LP Dr. Freada Kapor Klein with a single location at UC-Berkeley, SMASH has now served more than 1,000 students across 10 college campuses. Join us in donating here. 
  • Reimagining our deal flow. We’ve put measures in place to increase our deal flow from Black and Latinx founders in the enterprise. Among other measures, this includes working with Backstage Capital to increase underrepresented founders in our investment pipeline.

  • Offering training and assistance for portfolio companies. We’re developing resources to help portfolio companies drive inclusive practices from the ground up. Not only does starting from the beginning make diversity core to the company, it also generates better returns.

Who will you give to? How will you make your voice heard? Please consider investing your time, services, or money in a worthy organization that can affect long-term change.

Make these 6 words a daily practice 

Resolve to make a difference. Not only now in the wake of obvious tragedies and intense protests, but always. If you’re ready to put a permanent end to racism and discrimination, I hope you’ll keep these six words in mind Don’t wait, be intentional, give forward. 

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


Operator Spotlight: Verizon Media CTO Rathi Murthy

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 to Rathi Murthy, Chief Technology Officer at Verizon Media.

You just joined Verizon Media in January! What leadership lessons did you bring from previous companies that prepared you to lead in such a hectic, uncertain time? 

RATHI: When it comes to leadership, I like to remind myself of the 5 C’s. The first is Connect, or find time to meet with your teams to keep lines of communication open. The second C is Collaborate: share ideas and encourage new ways of thinking to reach solutions during this time. The third is Create, or innovate and build for changing conditions. The fourth C is Culture, make sure you keep a fun element in the work you do to maintain the feeling of belonging. And finally, Community: we can win together by helping and serving the larger community.

How has your Verizon Media team had to change because of COVID-19? 

RATHI: Fortunately, our teams were able to seamlessly adopt this new working-from-home style across most functions. In fact on our engineering side, we’ve seen no drop in productivity. That said, we’ve encouraged teams to meet on a regular basis and hold virtual stand-up meetings for status updates to maintain collaboration. Most critical, I think, is maintaining consistent communication from leadership. I post weekly video updates to help the team understand what leadership is thinking about during these times and how that affects their focus and priorities.

How has COVID-19 affected engineering teams in general? 

RATHI: We’ve challenged ourselves to find work we can do that will help during this time, which has given our team a unique drive to be creative and successful. For instance, given the vast amounts of data available about the disease and its spread, we saw an opportunity to use our big data expertise to create a searchable index of COVID-data that researchers can use to learn about trends. It was a massive undertaking for our team, but also such a rewarding project.

How has working remotely affected your operations? Do you have any lessons learned as we all start to think about a “back to work” structure? 

RATHI:  Verizon Media has technology at its core – and many of our engineers can work remotely, maintaining our technical performance. When we think about coming “back to work,” we are considering various aspects for what returning to the office might look like. We’re exploring how we can secure our facilities and make people feel safe once they are back in office, as well as working through how to manage social distancing and employee comfort with returning to the space.

What are some things engineering teams should prioritize over the next 6 months? 

RATHI: Leading with empathy, rather than emphasizing productivity. Remember that in this time, your team is dealing with many priorities, whether it’s childcare, educating children from home, caregiving for family members and pets, while also working. While productivity is important, it’s even more important to support one another during this time. 

Engineering is a profession that’s heavily dominated by males. What’s one piece of advice you’d offer other women looking to build a career in engineering and tech?

RATHI: Don’t let perfect be the enemy of the good. Speak up and take on opportunities even when you feel you don’t know 100% of what is expected. Grow your confidence and find your voice. We have a lot of advantages as women in our ability; we just need to believe in ourselves.

What’s one amazing insight no one knows about engineering?   

RATHI: Engineering is fun! There’s always something new, creative, and challenging coming up. It’s never stagnant. I’d love to bring this idea of “Engineering is FUN” to all the young women out there and encourage them to explore this field. 

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?

RATHI: I had children early in life – my early 20s. I started my Masters in Computer Engineering after my second child was born. When she was 1 month old. I had 2 kids under the age of 3 and started my journey to be a full time mom and study. I learned to be very disciplined, prioritize my work, delegate, leverage my family and friends for support, and manage myself efficiently. This foundation has helped me significantly. I also remember the kids falling sick the night before every exam. I had to be ready for any and all surprises. This has also been a good muscle to build, to handle curve balls with a smile. 

What’s one unconventional thing you’re doing to keep yourself sane?

RATHI: Peloton – I even take a few meetings while on the bike. It definitely keeps me sane 🙂

What’s the one condiment you could never live without? 

RATHI: I’d pick a spice, actually – Cumin!

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

SetSail with a unique take on sales productivity

The company: SetSail

SetSail offers a unique take on sales productivity, transforming complex data sets into simple, actionable insights. With this information in hand, sales organizations can easily pinpoint what’s working in their sales process and motivate reps to emulate those best practices. And the results are staggering: SetSail customers are seeing an average increase in revenue per rep of more than 15%. 

Why you should pay attention 

With a founding team from Google, the company is using advanced data science to help clients like Dropbox and Pendo bridge the missing link in sales productivity. Existing customer interaction data (such as email, calendar, and CRM) is analyzed by applying Machine Learning and Natural Language Processing on customer engagement signals. Unlike many AI-based solutions, the platform unlocks insights without requiring your data to be perfect. 

How it works

SetSail’s product starts by taking existing customer interactions, automatically capturing and enriching the data, and recording that back into your CRM system to create a solid foundation to build on. Their custom machine learning model peels back the layers on the data to identify and measure the real customer buying signals – such as interactions with key personas on particular topics like pricing or security. This helps companies move beyond basic activity metrics and rep-reported measures, gaining visibility into real deal progress. SetSail translates the best practices utilized by an organization’s top reps into a simple point-based sales incentive program. It even tracks performance and handles the payments. As clients’ business objectives evolve, the SetSail system evolves with them, providing a customized incentive plan (including SPIFs) that meets each team’s ideal sales motion. 

The context

Sales organizations are struggling as teams move to distributed models and reps are faced with a litany of choices each day on where to focus their time. In the last 5 years, sales ramp-up times, attrition rates, and the number of reps missing quota have grown tremendously. On top of this, sales leader tenure is down to just 18 months, leaving leaders scrambling to drive sales productivity gains on their own.

Why were obsessed 

SetSail is a first-of-its-kind Sales Behavior Management Platform that identifies best practices and helps leaders incentivize those best practices across their team at scale. SetSail is blazing a trail in delivering innovation that’s unlocking sales productivity and business growth for their clients. It’s truly a game changer.

Get involved

Turn your sales data into better productivity for your team today. Check out SetSail now to get started.

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

Top take-aways from The Challenge Series

We launched The Challenge Series in April to connect you with answers and advice from respected industry leaders as we manage our way through this pandemic. It’s been incredibly insightful to hear how some of today’s most respected execs are navigating the same issues we’re all dealing with ourselves, and we’ve been overwhelmed by the positive feedback from our community. In the spirit of sharing, we wanted to pass along some of our favorite lessons learned from the first three events, covering Operations, Marketing, and Finance. 

How do you shift your operations during a crisis? (Watch the replay)

We kicked off the series with a conversation with Cloudflare Co-Founder and COO Michelle Zatlyn and Gusto COO Lexi Reese, who offered sound advice on the operational issues facing companies today. These two respected leaders offered plenty of practical wisdom; here are a few of our favorite take-aways. 

  • Reel in your planning and budgets early. Much of the conversation focused on planning and budgets. Both Zatlyn and Reese acted quickly to trim budgets to the basics and must-haves only. According to Reese, “We threw out the idea of an annual plan. We have two priorities now: Keep our sector healthy and run operations way more efficiently.” Zatlyn added, “If you were tracking your business on a monthly or quarterly basis, you’ve got to move to weekly.”

  • Take care of customers and employees. Reese spoke several times about the importance of taking care of your community: “It’s not about having all the answers. It’s about being there for people when they need you.” She later added, “We had to make decisions and prioritize what enables us to earn customer love. That meant trimming and streamlining costs to help us weather this uncertain climate and emerge stronger.” Zatlyn echoed the feeling, saying, “In a crisis, leadership matters.” We agree!

  • Do what you can to come out stronger. Zatlyn also offered some inspiration in the form of advice. She recommended that companies focus on making changes to the business that will allow them to come back stronger after the pandemic, saying “Don’t get back to normal. Get back to better. Innovation comes out of these constraints.” In other words, take the time now to reassess your business and make changes that will help you flourish beyond the pandemic. Apply everything you’ve learned. Why go back to normal if your “normal” could use improvement? 

Marketing and messaging in the time of Coronavirus  (Watch the replay)

Zoom CMO Janine Pelosi and TripActions CMO Meagen Eisenberg have had opposite pandemic experiences – video collaboration has skyrocketed, while business travel basically stopped overnight. Both leaders offered excellent insights on how marketers can adjust their strategies and messages in a crisis. Here are a few of their practical tips.  

  • Build pipeline without being tone-deaf. Is this even possible? Eisenberg offers some advice: “Yes, if you focus on the educational material and the value you’re providing, and you’re not stretching what you provide. It’s not hardcore selling right now.” Now more than ever, authenticity is key. Create content and messages that offer genuine value and you’ll earn customer love, in addition to leads.

  • Break through the noise. Pelosi offered some great advice, saying “Attach yourself to something bigger, but in a way that’s authentic. Finding authentic ways to be relevant is key. Look at your partners and community, and don’t be afraid to send an ask.” Eisenberg pointed out that “we’ve seen some great things happening with creativity,” shouting out TripActions’ own #PassThePlane campaign. She also cautioned us to “think about your tone. We don’t need to be sad and depressed all the time – happy messages are welcome – but always consider your tone. If you’re unsure, test the message on five people before you send.” And Pelosi sums it up with: “For us, it’s all about metrics. Have the metrics set up so you can really understand the user voice. You have to track and understand sentiment not just in the good times, but even more so in the bad.”

  • Experiment with new tactics. Why not now? As Pelosi said, “The important thing is to pivot and change. All people knew was one element of marketing, and now they have to diversify. Education, telehelp, social try it all.” Eisenberg added, “We made a fast pivot to content that’s educational. People are re-educating, they want to come out stronger. Webinars are making a comeback. We’re trying to be smarter and more targeted with every message.”

  • Crisis communications call for transparency. Both leaders stressed the need for quick and honest communication. Pelosi says, “You have to stay true to who you are and to the core values of your company. You have to make the right decisions for the right reasons. If you try to candy coat something, it just doesn’t work. Surround yourself with the smartest people possibile and keep your eyes wide open.” Eisenberg chimed in with: “You have to be truthful and transparent. People put things out there that are not true, and the only way to counter that is to always be truthful. You have to be honest and even more transparent than you normally would be.”

  • A final piece of advice? According to Eisenberg, “Beyond mental health and wellness, every leader should be focused on customers and product-market fit. The companies that survive are the ones who have something that customers need. So keep checking in. Watch your usage stats and get your team focused on building what’s necessary to move forward.” 

How do enterprises manage their spend during a crisis? (Watch the replay)

Of course finance is top of mind in an economic downturn. Zendesk CFO Elena Gomez and Zoom CFO Kelly Steckelberg offered their insights and experiences with shifting budgets, managing priorities, and tracking metrics. Here are some key points. 

  • Where are you making cuts right now? This is a question on everyone’s mind, of course. Gomez said, “Our process at Zendesk is a bit surgical, but we look at which investments we want to preserve to maintain growth. We want to keep innovation, engineering, and the people who are selling and helping customers. And we inspect this on a regular cadence in case we need to course correct.”

  • What metrics should companies be looking at right now? Metrics have been a hot topic each week. With regard to finance, Gomez says, “Customer Acquisition Cost (CAC) will always be important in SaaS. We’re still very focused on renewal rates. The most important thing that drives your revenue is your currently booked business. Really the metrics haven’t changed as much as the cadence with which we look at them.” Steckelberg agreed, adding “Your core fundamental metrics should still be in place, even if they look different than they have historically.”

  • What does the world of M&A look like right now? Here Steckelberg offers positive news, saying: “We just made an acquisition completely via Zoom. In some ways this works even better. We were able to get it done quickly and quietly, and all via Zoom.” Gomez was more reserved, saying “We’re looking at the market opportunistically to see what would complement our offering but not any more or any less because of COVID-19.”

  • Advice for selling to the enterprise? Everyone wants to sell to the enterprise, but what’s the best way? Don’t shift your message. Steckelberg offers practical advice here, saying: “Don’t make whatever you’re selling about COVID. Make it about solving a larger problem. We hope COVID is short term in nature, so you need to give it a bigger perspective.”

  • Advice for finance teams: Echoing sentiments from our previous sessions, Gomez recommends to “take care of your customers – I can’t overstate that – as well as your employees. And make sure you’re ruthless in your prioritization.”

Huge shout out to our speakers and viewers, as well as to Zoom for powering our sessions. We’ve learned so much these past few weeks. Don’t miss this next event, Leading with Empathy and Kindness in Times of Uncertainty. Plus, thanks to an overwhelmingly positive response, we’ve added two extra sessions to the agenda Building Sales and Pipeline in a Downturn and How to Build a Customer-Centric Org. See you there!

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


Operator Spotlight: Partnerships Leader Bonita Stewart

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 to Bonita Stewart, Google’s Vice President of Global Partnerships.

You’re based in New York, where the COVID19 outbreak is severe. How do you balance your work with your well being and the well being of your team? 

BONITA: As a leader I have to prioritize the health and safety of my team above all else. A small group of my team members have created an activity series to simulate normal interaction – from virtual lunch sessions, to group Peloton rides (my favorite!), to a Netflix club. As they say, you can’t assist others until you put on your oxygen mask first. I stay grounded by attending my online ballet classes and remaining readily accessible to my team. I’m always a “ping” away.

You joined Google in 2006, so you’ve been there through several market downturns and natural disasters. How does your leadership change during these periods of uncertainty? 

BONITA: While I’ve definitely navigated challenging economic times throughout my career at Google, today’s reality is quite different. Situational leadership evolves each time to finding a level of precision, even when coupled with uncertainty. You must retain relentless prioritization of what you plan to do, what you are not going to do, and where you need to invest. It’s a constant dance of prioritization, problem solving, and creativity.

How has the COVID19 outbreak and market downturn affected the global partnerships realm? 

BONITA: Today’s climate puts my team front and center to bring both empathy and constructive business solutions for our partners. As a technology company, we often have a higher degree of fluency with technology-based solutions. So it’s critical for us to lead from the front to create comfort in new approaches.

How has working remotely affected your operations? Do you have any lessons learned as we all start to think about a “back to work” structure? 

BONITA: We’re pretty comfortable working from home, though working full-time from home is new. What I find most intriguing are the consumer habits we’re honing that will drive the new screen-based economy of the future. We shop online, pick up curbside, learn new skills via online learning, exercise with personalized trainers, and stream content along with traditional television. I can imagine a future where you can readily “tele-everything” – from medicine to shopping to apparel. 

What are some things partnership teams should focus on executing over the next 6 months? 

BONITA: Over the next six months, teams should focus on understanding consumer trends and identifying emerging business models. They have to become comfortable with experimentation. As partners work on fortifying their businesses, it’s important for partnership teams to support that effort by looking around the corner for technology-infused investment opportunities to fuel future growth. 

What’s one piece of advice you’d offer someone looking to build a career in partnerships and operations?

BONITA: While most partnerships evolve around business development skills, I’d recommend you develop expertise in understanding specific industries, their respective operations, and how they deliver economic value to consumers, shareholders, and employees.

What’s one amazing insight no one knows about global partnerships?   

BONITA: The possibilities are astounding. Our team works across multiple industries, with companies of all sizes around the world. In 2018, we shared more than $14 billion dollars with all of our publishing partners in our ad network. 

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?

BONITA: My most formative job was when I co-founded One Moment in Time, a company that specialized in formal wear rental for women. It was recognized in 1993 as one of the “hottest” businesses by Entrepreneur magazine. I learned what it really means when the buck stops with you, which extends to managing payroll, being scrappy, and re-booting when things don’t go well. It was the most exhilarating experience and laid the groundwork for expanding my risk profile. 

What’s the one condiment you could never live without? 

BONITA: Chipotle sauce from Stuart’s Seafood Market in Amagansett. It’s the best with scallops!

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


Simply binding: Why we’re crazy about Ironclad

The company: Ironclad

Ironclad is a digital contracting platform that industry leaders like L’Oréal, Mastercard, and Dropbox rely on to enable agile, collaborative, and data-driven contracting. By streamlining contract workflows from requests to approvals to storage, Ironclad creates a single source of truth for contracts and data. It is the only platform that handles every type of contract, no matter the use case or complexity.

Ironclad is proud to be a company that values diversity and inclusion. Almost half the company is female and 75% of the executive team are minorities or women. In 2019, Ironclad was featured on CloserIQ’s list of 10 San Francisco Companies with the Best D&I Programs. Read more about Ironclad’s commitment to inclusion, diversity, and culture here

Why you should pay attention 

Contracts are the atomic unit of modern business. Companies depend on successful contract management to drive relationships and mitigate risk.

But in today’s increasingly interconnected and rapidly changing world, the costs of contracting have never been greater. According to the IACCM, companies are losing 9.2% of annual revenues due to poor contract management. This doesn’t even take into account the opportunities lost to fragmented contracting processes or the cost of getting contracts done — $21,300 for a mid-complexity contract, and hundreds of thousands for a high-complexity contract. Ironclad enables businesses to be agile, efficient, and intelligent in managing every type of contract across departments. 

The details

Ironclad provides intuitive software that lets companies keep pace with the changing demands of modern business. Companies that fail to effectively manage risks or take advantage of new opportunities in today’s world risk getting left behind by competitors who have adapted better. Ironclad helps teams build and deploy scalable contract processes, work seamlessly with internal teams and counterparts, balance the need for speed and compliance, and make data-driven decisions from contract data.  

How it works

Ironclad lets customers build workflows for their contracts in minutes. 

  • Workflow Designer is a self-serve tool that helps legal teams create and enforce contract policies, without long implementation times or the need for technical expertise. With a straightforward drag-and-drop user interface, customers can build and launch contract generation and approval processes in minutes.
  • A full suite of collaboration and negotiation capabilities helps legal teams manage the contract redlining and revision process in one place — without forcing counterparties to do the same. 
  • Dynamic Repository is the only user-friendly, enterprise-grade contract repository in the contract management space.

Why were obsessed 

Especially during times of uncertainty, legal teams play a crucial role in helping businesses navigate risk and survive. Ironclad is not only a contract management tool, but also a comprehensive platform that lets legal teams collaborate remotely, maintain data integrity, and get the answers they need in seconds. Whereas onboarding and integration with standard contract management tools can take months, Ironclad’s team of experts in legal workflow and technical implementation helps customers onboard and iterate quickly. They are on track to become the leading trusted provider of legal software.

Get involved

Interested in the digital transformation of legal? Join Ironclad’s community of legal professionals to access events, webinars, and monthly newsletters and see how the product works.

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


The Challenge Series: Adding inclusive voices to the COVID response

Global pandemics wreak their own special kind of havoc — not just on our health, but on virtually every aspect of our lives. Solving something as massive as a global health emergency takes a coordinated, collaborative effort and requires us to put our best minds forward. That means not just in frontline healthcare and government response, but also in education, recreation, nonprofit, and business. 

In times of crisis, leaders emerge. We’re all looking for answers and guidance. It’s widely understood that diverse teams lead to greater innovation, better outcomes, and more progress, so we cringe every time we see photos and events featuring homogeneous teams and panels in response to today’s challenges. (As it turns out, we’re not the only ones to notice.) The representation has improved recently, with women in leadership roles receiving kudos for how they’re handling their COVID-19 responses in federal governments, local governments, and science. Now we’re ready to add to that list from a business perspective.  

Join us for the Challenge Series

Introducing The Challenge Series, weekly online events designed to connect you with the specific topics and advice you need. Businesses are scrambling to address challenges they couldn’t have imagined just a month ago. As we work to keep our teams and companies going, it’s helpful for all of us to hear how some of today’s respected leaders are navigating similar issues. We’ve assembled an incredible line-up of speakers who are leading their companies through this time — and this first group happens to be all women. How are they shifting their operations, marketing, and finance? How do they lead with empathy and kindness through scary situations? Join us weekly to find out.

Learn how experienced executive leaders at companies like Gusto, Cloudflare, Zoom, Zendesk, Guild Education, TripActions, and Textio are shifting their models, protecting their budgets, and supporting their employees through every stressful moment. Got a question or two for these leaders? Please share with us on Twitter or LinkedIn and we’ll add them to the queue. 

Upcoming Challenge Series Events

  • April 28: How do you shift your operations during a crisis? (REGISTER)
  • May 5: Marketing and messaging in the time of Coronavirus (REGISTER)
  • May 12: How do enterprises manage their spend during a crisis? (REGISTER)
  • May 19: Leading with empathy and kindness in times of uncertainty (REGISTER)

Staying ahead of these situations requires diverse, inclusive voices

Scientists predict additional waves of COVID-19 and a rise in similar viruses in years to come. As we determine what that means for not only healthcare, but businesses, the overall economy, and even day-to-day human life, we ask organizations to prioritize diverse, inclusive voices in their preparations and responses. Put women and underrepresented minorities in leadership roles; listen to their voices. Make them not the exception, but the norm. Excluding these portions of the talent pool limits our collective ability to innovate and respond to the spidering effects of these situations. 

Here at Operator Collective, we’re lucky to have a community packed with talented, experienced leaders, the majority of whom are fearless women. We look forward to sharing their insights with you. Learn more and register for The Challenge Series here

The Challenge Series from Operator Collective


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


3 CFO tips for adapting your finances in a downturn

Market volatility wreaks havoc on companies, especially those early-stage, VC-backed ones. If your company is under financial distress, the first thing to do is reexamine your operating plan. It’s vital to adapt and course-correct now in order to plan for the remainder of 2020 and get ready to scale. Let this be your call to action: The ones who adapt are the ones who survive. 

VC-backed companies run on tight timelines. They’ve got milestones to achieve, customer relationships to build, and products to sell. Given these competing priorities, building a solid annual financial plan may not be top of mind. However — and I can’t emphasize this enough — you must have a solid operating plan to serve as your compass right now. With that in mind, here are three tips to help you adapt your finances in a market downturn. 

1) Engage in scenario planning

As the name suggests, you’ve got to have multiple plans driven by their outlook on the sales forecast. In the B2B SaaS world, revenue forecasting can be done from the bottom-up (rolling up all pipeline customers, your best thoughts on deal size, and timing of closure) or top down (capacity planning based on the time to ramp up and execute against quota and attainment). In fleshing out these forecast, one should keep in mind trigger events:

  • Changes in product demand 
  • Changes in customer situations 
  • Customer up or down shifts
  • Shifts in funding situations

I always caution against putting $0 sales forecasts, even in the darkest of the hours. The downturn guidance for revenue revision is 30-40% from the previously approved operating plan. If you’re starting from scratch, please be sure to add your views and action plans on how to bridge the gap between pre-COVID-19 and post-COVID-19 forecast; it does not need to be precise, but it’s a good way to frame the CEO’s view on the outlook of your product.

Scenario planning gives the team more flexibility to manage expenses, plan for headcount, utilize other financing options, and shift budget modes when trigger events take place. 

2) Move to zero-based budgeting 

Most budgets start with historical expenses and sales forecasts, then take the incremental growth % to execute the top line. In zero-based budgeting, however, companies build their forecasts based on what is absolutely needed to support their sales forecast and drastically rethink their business models. 

Zero-based budgeting works well when a significant investment lies ahead, but the near-term sales forecast is lower than what the original operating plan indicated. This method allows operators to prioritize their spending needs, but not be bound by historical spending. It also gives a drastic view on meeting competing priorities by categorizing expenses as keep, stop, or modify. 

  • Keep expenses: These are your vitals, like payroll, hosting fees, utilities, and rent. If possible, revisit the contracts you have with long-term partners to find fair updates.
  • Stop expenses: These are unnecessary costs. Billboard advertising, for instance, is no longer wise given our stay-at-home orders. Unwind these contracts to stop the bleeding.
  • Modify expenses: These are expenses that are still needed, but at a modified capacity. Things like new hires, marketing agency fees, and legal fees fit in this category. 

3) Practice financial discipline  

In early-to-late stage companies, monthly budget execution adds great operational discipline. For instance, Operator Collective sets a monthly budget they need to spend up to for each department, which then resets every month. For this to happen, each department needs to track expenses at the invoice level. 

This may feel like a lot, but once you set the process in motion, it works. This is not only about fiscal discipline and transparency, though — it also provides a venue for people to discuss their plans and adjust as needed.

Bottom line: You’ve got to have a solid budget and operating plan 

In today’s volatile economy, your budget is obsolete the moment it’s complete. So what’s the point of going through these processes? 

Having an Annual Operating Plan serves as the proverbial “line in the sand” for management, employees, and the board. It offers a tangible way to track performance, calibrate, and course-correct. For this reason alone, budgeting is a worthwhile exercise, with the caveat that operators should treat it as a living organism, instead of putting the operating plan on the shelf to gather dust, only to be seen in a quarterly board meeting. 

Once your Annual Operating Plan is in place, it’s wise to break it into mini-milestones and quarterly plans to execute and track against actual. Set up a dedicated, recurring regular meeting to align at a cadence that makes sense for your team. Start with a high frequency, then adjust as people become familiar with the practice. This sounds daunting, but it can be done in a simple Google sheet by listing out high level forecasts vs. actual performance. In doing so, your company will garner insight into the operation and results, and can use the information to plan better for the future and react as unexpected events occur.

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