How your sales team can Outreach, outlast, and outperform

The company: Outreach

Outreach delivers a sales engagement platform that helps sales professionals engage with customers to grow their revenue faster and more predictably. Outreach is changing the game for revenue teams everywhere and redefining how companies engage with their customers throughout the lifecycle. 

Why you should pay attention 

Outreach is the category leader in the fast-growing Sales Engagement space. The company earned its spot on the leaderboard by inventing transformative changes that help their customers dramatically increase sales productivity and drive smarter, more insightful customer engagement. The platform delivers a jaw-dropping 387% ROI with a 5X return on investment for its more than 4,000 customers (which include companies such as Adobe, Tableau, DoorDash, Splunk, DocuSign, and SAP). 

The details 

At the core of Outreach is a system of action that gives sales reps insights and recommended activities to close deals quickly and effectively. The system uses AI and machine learning to help sales reps reach clients and prospects on their own terms, working across email, social, voice, and text-based communication methods. Outreach even allows them to test different messages and approaches in order to optimize the content and improve their outcomes at scale. And how do you know what works? Simple: Reporting functionality gives visibility into sales rep activity so team leaders can see what performs and what doesn’t. The platform then delivers the insights everyone needs to stay focused and deliver a simplified, consistent experience across all stages of the sales cycle.

How it works

Outreach’s customer engagement platform gives sales teams the tools they need to choreograph an engaging, personalized buyer’s journey for each of their customers and prospects. It drives new levels of efficiency and visibility into the sales system. From saving reps hours of work to driving messaging alignment and ROI and growing the pipeline, Outreach’s customers are using the platform as a playbook for success and revenue growth.  

Why were obsessed 

Outreach is on an incredible trajectory because it is delivering immense value to clients, which include a who’s who of everything from the hottest tech startups to the F100 icons. That’s reflected in its valuation: The company has officially become a “unicorn,” valued at $1.3+ billion — the only company in the dynamic sales engagement space with that mythical status. The company leads its sector because it’s driving breakthrough innovation that fuels exponential revenue growth for its thousands of clients. It’s easy to see why we’re obsessed. 

Get involved

Ready to make your team a revenue-driving machine? It’s time: Get Outreach.  

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.

Words matter: Textio makes business writing more effective and inclusive

The company: Textio

Textio is an augmented writing platform that’s changing how companies work. Using language patterns and data insights, Textio helps companies be more intentional with their business writing so it has the impact they intend. At the most basic level, Textio gives businesses new ways to transform their company culture by innovating on the most powerful tool that every human has to affect change: the words we use to communicate.

It’s how you say it

The words your company uses everyday broadcast to the world what your company values. Companies like Nestle, McDonald’s, and Zillow turn to Textio when they want to get more intentional about the alignment between their words and their culture. Textio also helps ensure business language appeals broadly and is inclusive across gender, age, and ability and optimized to get a response. Apple, Cisco, Johnson & Johnson, and NASA use Textio daily to make sure their values and culture shine through in their most critical communications.

The details

Think of Textio as a word processor that’s designed to predict how readers will respond and engage based on the patterns of language that are being used. The words in a job description, for example, can profoundly affect the profile of the candidate pool that applies, which in turn is a reflection of the employee base. Companies use Textio to ensure their business communications are more inclusive, deliberate, and impactful. The platform is highly instrumented to provide data and insights that flag jargon, make suggestions, and even reveal gender-coded language that the writer may not see. Textio lives at the intersection of creative writing and breakthrough innovation. That’s reflected in the credentials of its top leaders: CEO Kieran Snyder has a PhD in linguistics and cognitive science, and both she and her co-founder Jensen Harris held leadership roles at Microsoft before starting Textio.

How it works

As you’re writing, Textio is comparing your language to its vast databases of more than 600 million documents to parse the most relevant and make recommendations on language patterns that are proven to work well in a given situation. The platform continually evolves and improves via a learning loop — each user of the system makes the platform more intelligent. Textio makes predictions on who will engage with the content as it’s being written, it makes suggestions for changing something that’s just been typed, and it proactively creates language to help achieve the recruitment, corporate culture, or digital transformation objectives the business is working towards.

Why we’re obsessed

Diversity and culture are key imperatives for Operator Collective and we have high standards for this in the companies we invest in. Textio is building innovation that helps more companies create inclusive cultures, foster diversity, and build belonging.

Get involved

Now more than ever, businesses recognize that inclusion is an imperative. Meet Textio, and make your words matter.

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

 

20 books to add to your reading list

You’re always wishing you had more time to read, right? The COVID-19 social distancing mandate could be your chance. In case you need a little inspiration, we asked our community to share their favorite books with us. Here we’ve compiled a list of suggested fiction, nonfiction, and memoir selections. Perhaps you’ll start with that best-seller you’ve heard so much about or an easy beach read to take a mental vacation, or maybe even a cult classic you’ve always meant to grab. Enjoy!

FICTION FAVORITES 

The Dutch House by Ann Patchett. When two wealthy siblings are exiled from their home at an early age by their stepmother, they’re thrown into poverty. Relying on each other, they overcome desperate situations, yet never stray far from the orbit and draw of their eccentric childhood home. (Leyla Seka)

Some Love, Some Pain, Sometime by J. California Cooper. This collection of short stories offers up a diverse cast of characters that often struggle to make the right choices and find happiness in a society that often chooses light skin over dark and money over spirit. Each episode inspires, though, bubbling over with laughter, advice, and enjoyment. (Molly Ford)

A Tale for the Time Being by Ruth Ozeki. Nao is a 16-year-old who’s uprooted from her life in California to return to Japan when her father loses his job. To overcome her suicidal thoughts, she decides to research and write the story of her grandmother, a Buddhist nun. Ruth is a novelist on an island off the coast of Canada. When Ruth finds a Hello Kitty lunchbox washed up on shore, she’s thrown into the mystery of Nao’s life. (Jenny Sohn)

The Alchemist by Paulo Coelho. This novel tells the mystical story of Santiago, a shepherd boy who longs for adventure, travel, and wealth. His quest leads him to riches far different and more satisfying than he ever imagined. His journey serves as a grand reminder to seize opportunities, recognize the omens in life, and follow your dreams. (Lolita Taub)

Play It as It Lays by Joan Didion. This classic novel chronicles the Hollywood subcultures of the 1960s via the downward drift of a particular actress. In concise-yet-stunning language, the book captures the ennui of society and remains more than three decades after its original publication a profound read, riveting in its exploration of a woman and a society in crisis. (Erica Schultz)  

The Lymond Chronicles series by Dorothy Dunnett. Romp through history with incredible detail, plotting, maneuvering, travel, costumes, suspense, and hilarity. In 1547, the disgraced Francis Crawford of Lymond embarks on a fantastic journey to redeem his reputation. Follow along as his quest takes him from decadent French Courts to the battlegrounds of Malta to the hidden palaces of the Ottoman Empire and well beyond. (Laura Butler)

Beneath a Scarlet Sky by Mark Sullivan. As an Italian teenager during World War II, Pino Lella was drawn into helping Jews escape over the Italian Alps to Switzerland, then led a double life as driver to a German general and spy for the Allies. If this book were pure fiction, readers might regard it as too far-fetched, but the fact that it recounts actual experiences makes it captivating. (Meagen Eisenberg)

Where the Crawdads Sing by Delia Owens. In the outer banks of North Carolina lives the “Marsh Girl,” Kya Clark, who survived for years alone in the marsh that she calls home, finding friends in the gulls and food in the sand and ocean. When a local boy is found dead, the town immediately suspects Kya, but her mysterious life is not what it seems. (Robin Joy)

Jack Reacher novels by Lee Child. Jack Reacher is a former Major in the United States Army Military Police Corps. Though he has a shady past, he maintains an in-depth sense of what is right. The series follows him as he falls into webs of complications and mysteries. These books are plentiful and not published in a chronological order, which means you can pick and choose as you like. (Elisa Steele)

RIVETING MEMOIRS 

Year of Yes by Shonda Rhimes. She’s the creator and producer of some of the most audacious shows on TV, yet Shonda Rhimes is a classic introvert, avoiding public appearances and suffering panic attacks before interviews. When her sister points out that you never say yes to anything, Shonda chose to make a change, challenging herself to say YES to everything that scared her for one year. (Anita Lynch)

Born a Crime by Trevor Noah. You might know Trevor Noah as the affable host of The Daily Show, but his path to success was everything but easy. Noah was born in apartheid South Africa to a white Swiss father and a black Xhosa mother at a time when such a union was punishable by five years in prison. This is his tale. (Lisa Campbell)

Molly’s Game by Molly Bloom. For a time, Molly Bloom ran the most exclusive poker game in Los Angeles. She staged her games in hotel suites, dined at exclusive restaurants, flew privately, and hobnobbed with celebrities, until it all came crashing down. This is a behind-the-scenes look at Molly’s game, the life she created, the life she lost, and what she learned through it all. (Elena Gomez)

Maybe You Should Talk to Someone by Lori Gottlieb. Thanks to the nature of their work, many therapists see their own counselors. But when an unexpected breakup leaves her reeling, therapist Lori Gottlieb enlists a new counselor to help her work through her issues. Gottlieb is hesitant at first to open up to “Wendell” (a middle-aged, balding man in a cardigan), but his odd methods make an impact. (Erica Dorfman)

Tokyo Vice by Jake Adelstein. An American investigative journalist takes on Japanese organized crime, but when one scoop exposes a scandal that results in a death threat for him and his family, he decides to step down. Here he delivers an open look at Japanese culture and searing memoir about his rise from cub reporter to seasoned journalist with a price on his head. (Nicolas Dessaigne)

Look Alive Out There by Sloane Crosley. This collection of essays is a deep yet humorous take on the catastrophes of everyday life. It’s like “listening to your smartest, funniest friend regale you about their (mis)adventures, be it waging war on a rude neighbor, making an ill-conceived climb up a volcano, or helping a swinger couple pick out a third.” (Ambrosia Vertesi)

GRIPPING NON-FICTION 

Team of Rivals. Award-winning historian Doris Kearns Goodwin shines a light on Abraham Lincoln’s true political genius in this highly engrossing work. Enjoy the research as the one-term congressman and prairie lawyer rises from total obscurity to prevail over three gifted rivals of national reputation to become president. (Anirma Gupta)

Tightrope: Americans Reaching for Hope by Nicholas Kristof and Sheryl WuDunn. This book weaves together eye-opening stories of children growing up today in an “other America.” As a whole, these detailed accounts show how working-class families have been all but forgotten as a result of decades of policy mistakes. (Reshma Saujani)

The Short and Tragic Life of Robert Peace by Jeff Hobbs. When Jeff Hobbs arrived at Yale, he met the man who would be his roommate for four years: Robert Peace. Robert grew up in the crime-ridden streets of Newark in the 1980s. The brilliant Robert studied molecular biochemistry and biophysics, but is unable to fully leave street life behind him. (Ebony Beckwith)

Beginning of Infinity by David Deutsch. Physicist and author Deutsch talks about the unlimited nature of human progress and how we often underestimate our ability to find solutions to problems. He argues that explanations have a fundamental place in the universe—and that improving them is the basic regulating principle of all successful human endeavor. (Nick Mehta)

The Boys in the Boat by Daniel James Brown. This must-read tells the story of the University of Washington’s 1936 crew team on an epic quest for an Olympic gold medal under the watchful eye of Adolf Hitler. The rag-tag team, sons of loggers, shipyard workers, and farmers, remind us that victory is possible when everyone literally pulls together. (Ruthie Miller)

More suggestions to maintain your #PositiveOps

Looking for more fun recommendations to keep things positive while sequestered at home? Here are 30+ at-home activities to keep you physically and mentally fit. And here are 8 podcast recommendations to entertain and distract.

How are you staying positive these days? We’d love to know — Please share your recs with us on Twitter at @OperatorCollect.

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

8 ways our community is fighting COVID-19

As the world works to contain the COVID-19 outbreak, our own community has gone into overdrive. We’re so proud of our Operator Collective LPs for leading this charge. Here are some of the ways they’re using their platforms, tools, and networks to help. 

  • Eric Yuan, Kelly Steckelberg, Janine Pelosi Zoom
    In today’s everything-from-home economy, Zoom has become the de facto tool for communications, virtual meetings, remote work, family chats, and more. But what about our schools? As educational institutions shut down around the world, the Zoom team truly stepped up, offering its video conferencing tool free to any K-12 school.

  • Rachel Carlson Guild Education
    Rachel Carlson has emerged as a persuasive voice in the coronavirus crisis, imploring her fellow business leaders to #StopTheSpread. She co-wrote a letter imploring Americans to take “bold action” to slow the spread of the coronavirus, and then a more direct ask to corporate leaders. By circulating the letter, Carlson hopes business leaders can remove some of the burden from local, state, and federal governments.

  • Kimber Lockhart One Medical
    One Medical is a membership-based primary care practice. In addition to offering same-day appointments, providers offer 24/7 video visits. One Medical has also created a Coronavirus Help Center with resources to help everyone stay up to date with the latest information.

  • Nihal Mehta – Eniac Ventures + Reshma Saujani – Girls Who Code
    Nihal Mehta recently launched Help Main Street, a crowdfunded platform to keep shops, restaurants, and industry workers afloat via gift card sales. Want to help your local favorites? Go to helpmainstreet.com to purchase gift cards to provide critical cash support during the COVID-19 outbreak.

  • Jennifer Tejada – PagerDuty
    PagerDuty is a platform that helps companies manage the full spectrum of their digital operations. As healthcare organizations struggle with demand and stress, they need to stay prepared and “always on.” To that end, Tejada and PagerDuty recently announced an offer for healthcare organizations: 20 PagerDuty licenses free for six months.

  • Christina Kosmowski Slack
    Slack has seen huge increases in paid customers since the coronavirus outbreak, offering plenty of content to facilitate remote working (including this Guide to Working Remotely in Slack). They’ve also announced free upgrades to teams working to solve the crisis.

  • Michelle Zatlyn – Cloudflare
    Cloudflare accelerates Internet properties, helping businesses stay productive from any location. Early in the coronavirus outbreak, Zatlyn and team made their enterprise-grade features available to small businesses at no cost, offering unlimited seats of Cloudflare for Teams through September 1.

  • Lexi Reese – Gusto
    Gusto is an automated platform for payroll, HR, and employee benefits, aimed specifically at small businesses. They’ve recently launched a COVID-19 Resource Hub to offer small businesses the most updated news, information, and advice.
We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

It’s uncomplicated: Why we’re crazy about DataGrail

The company: DataGrail 

DataGrail is a privacy platform that simplifies compliance with GDPR, CCPA, and similar privacy regulations. In this Age of Privacy, DataGrail is helping companies stay in line with regulators while building trust with their customers by driving new standards of transparency and accountability. 

DataGrail was built on the principles of diversity and inclusion from the very beginning. About 40% of the company is female (a percentage which has never been below 30%), 50% of the board members are female, and 11% of employees identify as LGBT+ or gender non-binary. Read more about DataGrail’s commitment to supporting workplace diversity in their recent blog post.

Why you should pay attention 

The rapid-fire expansion in privacy regulations combined with the dramatic explosion in data collection is creating major turbulence for businesses. The average enterprise has 88 different systems that could contain personal data, and Gartner predicts that by 2023, 63% of the planet’s population will have GDPR-like personal data protection (up from 10% today). Yet DataGrail’s recent consumer survey shows 83% of Americans expect to have control of how businesses manage their data. Companies clearly need help navigating this landscape, and DataGrail is leading the way.

The details 

The issue is clear: privacy is a fundamental human right and essential to democracy. So in 2018, Daniel Barber, Earl Hathaway, and Ignacio Zendejas launched a business built on this covenant of trust. With 200+ pre-built connectors, the DataGrail Privacy Platform gives a 360-degree, real-time view of the applications a business uses, then maps personal data associated with each of those systems. Customers can manage their privacy request workflows and email preferences across applications.

Building trust through transparency. Taking complicated out of compliance. DataGrail is changing the game.  

How it works

At the core of the solution is DataGrail’s Live Data Map, which provides a continually refreshed blueprint of where data lives in the organization. Any changes made to the systems are reflected automatically. Privacy requests are streamlined, eliminating human errors and reducing risk. And DataGrail’s hundreds of pre-built integrations (Salesforce, Adobe, Oracle, AWS, and more) streamline the onboarding process, making data discovery almost instantaneous. This makes sure companies not only achieve compliance, but are continuously compliant over time as regulations change externally, and business systems, fields, and owners change internally.

Why were obsessed 

Today trust is a currency, and DataGrail is here to help companies grow and manage this business-critical resource. DataGrail clients like Overstock.com, Restoration Hardware, Revolve, Databricks, and more rave about how the company helps them manage data privacy risk and compliance (simplicity, automation, and real-time insights are the common refrains). By taking on the complexity of the continually shifting regulatory landscape, DataGrail is simplifying compliance and helping its clients stay ahead of the curve. 

Get involved

Ready to supercharge your company’s privacy disciplines? Let DataGrail handle your compliance needs. Get started here now. 

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

5 tips for building a thriving community from scratch

Those pics up there? That was me when I was a kid. I was the third of four children born to immigrant parents who still don’t speak much English. We were just trying to make ends meet, and life was pretty simple – food, school, and of course piano.

American ways were quite foreign to us. I still have to make my fingers into a “b” and a “d” to figure out where my bread plate and drinking glass go, and I was told Westerners weren’t trustworthy since they often said things they didn’t mean, like “Let’s have lunch” and not follow through. Or “How are you,” but not wait for an answer.

In 8th grade I was 4’6” with a home perm, heavy bangs, and thick glasses. We didn’t have much money, so I had three outfits; I wore each for two days in a row before rotating. There are kids who don’t mind these “limitations,” but I wasn’t one of them. I desperately wanted to fit in, but this was tough: even beyond my awkwardness, I was pretty unremarkable. I’m one of the few people I know who had virtually no activities in high school (I do know every episode of Gilligan’s Island, though). Plus, as with many families back then, parents didn’t talk about “adult things” to kids. All this means I didn’t really begin to interact comfortably with adults until I was about 30. 

Fast forward to today: I’m on my fourth startup, all of which have incredibly strong communities with networking that’s core to their success – ChIPs (5,000 members and 19 chapters around the world), RPX ($0 to $100M and IPO in less than three years), SaaStr (world’s largest b2b software community), and Operator Collective. How does someone so socially awkward build such thriving communities? In many ways not being a cool kid growing up was the perfect training ground for constructing communities and building startups. Here are five tips.

1) Find your niche

Communities and products succeed because they have a focus. People need a personal connection, which might mean choosing an area that’s ignored or overlooked. ChIPs started out hyperfocused on women in patent law (there weren’t many of us). Only after nailing that niche did we expand to women in law, tech, and policy. The venture world typically revolves around VCs and founders – so at Operator Collective, we put operators front and center.

Think about my awkward former self who just wanted to fit in. What if I’d had a community of Gilligan’s Island Aficionados Who Love Velour? I would’ve fit right in and had a core group to identify with. Find an initial niche or addressable market and expand from there.

2) Start with the bellwethers

The first thing everyone wants to know is who’s involved. Having not naturally been a people magnet, I learned to involve the people others do want to hang out with, and build from there.

If you’re hosting a conference, the obvious way is to begin with the speakers. Find an anchor and build around her. How do you get that first speaker? Try starting with a “two-fer” – find two speakers with a connection or friendship. If someone can combine a speaking engagement with seeing people they don’t often get to spend time with, they’re more likely to say yes. At Operator Summit, we invited fantastic speakers, but paired them each with a friend – like Eric Yuan with Jennifer Tejada, and Claire Hughes Johnson with Leyla Seka. This also applies when building a customer base: Garner a few respected companies/leaders as early adopters.

3) Be deliberate from the first engagement

You always have to make people feel comfortable – including those who don’t often join in. Last September, we put together Operator Summit in just 4 weeks. We knew we wanted a high percentage of women and people from underrepresented backgrounds, so we were public with that intention and deliberately reached out to people in those categories. It wasn’t a women’s conference or one for people of color, but we ended up with 80% women and 50% people of color.

This was another place being socially awkward helped. What would it take to get me to come to an event that’s full of people I didn’t know? A personal invitation, first of all – not a bulk mailing. Plus we asked those who were coming for names of contacts who might be interested, and then specifically mentioned the referring friend in that invitation. By the time you get to a SaaStr Annual size of 20,000 attendees, personal invitations aren’t always possible, but you can still do it selectively. The same goes for selling a product. Each interaction should feel personalized, so every prospect gets the sense that you are connecting with them as an individual and understand their needs.

4) Make it easy to participate

When you’re selling a product, you make it easy to buy. When you’re putting together a community, you make it easy to join. Start with scheduling. We have a lot of women with young kids in our Operator Collective community, so we try to schedule meetings and events at family-friendly times. Operator Summit, for example, started at 10 and ended at 4:30. When we have update calls, we try to schedule them for when we know people have finished dropping off kids at school, over lunch, or during a commute time. If we’re scheduling a group, we’ll often send a poll to ensure a critical mass.

The other key is to give people a role. It can be scary to walk into a new meeting or conference, so introverts like me prefer to have a task. At SaaStr Annual, “braindates” are wildly popular. At Operator Summit, we encourage people to sign up for our small group Office Hours.

5) Obsess over every detail

No matter what you’re building, you can never assume people will buy, join, or participate. You have to make it worthwhile, which means obsessing over every detail. What’s the mix of people, who will they meet, and what will make them come back? What kind of content will you provide and where will everyone find value? What’s the reg process, what about dietary restrictions, and what kind of swag? Obsess over every detail, from how they buy to how the product is delivered to the entire user experience.

Get Building

From the day we enter the working world and actually well before the need to network is hammered into us. We have to put ourselves out there and expand our connections in order to advance our careers. But communities can be a haven for the socially awkward: a place for people to find their niche and feel comfortable. And if this kid can grow up to be a super connector who builds successful network-dependent companies, I’m here to tell you that anyone can.

P.S. If you want to see my awkwardness in action, join me on March 11 at SaaStr Annual, where Leyla Seka, Lexi Reese, Elisa Steele, and I will do battle in an unscripted debate to determine the #1 secret to building high-performance orgs. I’m terrified already. 

The outsiders are coming in: The origin of Operator Collective

For most of my life, I’ve felt like an outsider. Whether it was being raised by immigrant parents who didn’t understand Western social norms, or my years as an awkward kid picked last for everything, or being one of the few women Chief Intellectual Property Counsels in the niche-y field of patent law, I’ve always been most comfortable working quietly in the background.

When you’re an outsider, you spend a lot of time observing. I’m often told I think outside the box, to which I silently respond it’s because I’m not enough of an insider to even know what the confines of the box are. And when you’re an outsider, you sometimes don’t even realize you have skills that would be useful to others.

Here’s an example. In 2008 I helped launch a venture-backed company we took from $0 to $100M and IPO in three years but I was such an outsider to venture that I didn’t realize this was unusual. There were the inevitable and valuable lessons learned during that period, and we ultimately grew the company to $300M.

After we sold the company ten years later, I started to spend more time with founders and VCs, mostly as part of the SaaStr community, which I’d been involved in from the early days (I’m married to the founder). And of course, I spent a lot of time where I’m most comfortable quietly observing. Here’s what I saw:  

  • The venture world revolves around VCs and founders. 
  • Roughly 90% of VCs and founders are white males, higher when you look at enterprise.
  • VCs and founders tend to hang out with other VCs and founders, and their networks don’t overlap much with operators, much less with women operators. 
  • Most b2b startups eventually want to sell their products to enterprise.
  • The majority of VCs and founders have either never worked in enterprise, or haven’t done so in decades.  

As I began to dip my toe in angel investing, I noticed something else: I was often the only woman on the cap table, and homogeneous groups were showing up again and again. I was bothered enough to ask a few founders if they’d noticed. These founders, to their credit, were horrified, and then even more distressed when they realized they hadn’t recognized it prior to my asking the question. They explained that they’d simply gone to their buddies for backing they didn’t know any women who might invest and could I please help.

The Buddy Syndrome strikes again
The fact is, they weren’t wrong. When you’re in the early days of starting a company, you turn to people you know the ones who trust you and are willing to take a chance. And people from your network tend to be people like you. (I call this the buddy syndrome.)

And beyond this, it’s a fact that fewer women invest. Women hold 71% of their assets in cash. They make up just 9% of venture decision makers and 22% of angel investors. And if you focus only on my area enterprise the numbers drop even more.

At the same time, I began asking my women friends: “Why don’t you angel invest?” Never been asked. Never had the opportunity. Didn’t occur to me that it was a possibility. No time to vet and not sure I know how to vet anyway.

Why aren’t more women investing?
I heard this over and over and from some of the most accomplished operators in the world, many of whom happened to be women… leaders who’d built the most successful tech companies in the world. In fact, many of today’s most respected operators are women.

Earlier this year one of our LPs, Reshma Saujani, Founder & CEO of Girls Who Code, released her book Brave, Not Perfect; this is based on the idea that from a young age, boys are praised when they take risks, while girls are expected to be perfect and steer clear of taking chances. Saujani’s experience is in the world of coding, but the translation to enterprise is clear: Women today are conditioned to be perfect at work, at home, and frankly in everything we do. As a result, we give 150% to our day jobs and 150% to our family and friends. We’re not looking to meet VCs and founders in the little time we have left over. Sprinkle in the gender pay equity gap and “gap table,” and the result is that most women don’t have the liquidity, much less the desire, to invest in people they don’t know and in startups they don’t have the time to vet. Yet they’re the very people with the backgrounds the venture world could use. So these women these ultra talented operators were also outsiders with no obvious path to get in.

On the flip side, there’s venture. Now the value of diversity has been well established, yet venture remains homogeneous not because no one wants the change, but because there hasn’t been a natural way for it to happen (birds of a feather, and all that). So what we wanted to do was help both sides of the equation: Give talented operators from diverse backgrounds a safe, comfortable way to join venture + make it easy for founders and VCs to bring in new experience and perspectives.

The origin of Operator Collective
The idea took hold quickly. Operators were thrilled at the idea (just look at the absurd amount of talent we’ve assembled), and they quickly referred their fellow operators. Even universities and foundations signed on as LPs, a rarity for a first-time fund. And of course as we operators have been trained to do, we built this fund to have immediate product-market fit to address that gaping lack of operational expertise in venture.

So here we go. The sidelines are bursting, and the outsiders are coming in.

Say hello to Operator Collective.

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

Infographic: The absurd amount of talent in Operator Collective

It’s no secret venture capital is an exclusive and homogeneous group that’s hard for outsiders to crack. Yet VCs and founders don’t build companies — operators do. So why don’t they have a bigger voice to decide which founders get funded and how they’ll be supported?

That’s why we created Operator Collective, a new venture capital fund with a community of ultra-talented operators built right into its DNA. Operator Collective is making venture accessible to exactly the people the ecosystem needs now: leaders from diverse backgrounds with deep experience from building some of today’s most successful companies.

Our limited partners include 100+ respected operators who bring decades of experience growing and running the world’s most admired companies — from Zoom, Stripe, and PagerDuty to Salesforce, Slack, and beyond. They have more than 1500 years of collective operator experience; more than 60 of our LPs have built unicorns, more than 35 have taken their companies public, and more than 80 have steered their companies through acquisitions. The amount of revenue they own and people they lead is staggering.

Learn more in the graphic below. What an incredible team to have on your side.

Operator Collective Infographic

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