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.


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!


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)


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)


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 or on Twitter and LinkedIn.

Amid a diversity gap in the VC world, Operator Collective creates a new model

Mallun Yen

This article by Teryn O’Brien was originally published on

Diversity in the workplace provides benefits that aren’t usually seen in a group of like-minded people, including increased innovation and creativity, higher employee engagement and lower turnover. Unfortunately, diversity in gender, race, age and other demographics still isn’t a feature of today’s venture capital world.

Continue reading here.

Operator Collective is a diverse group of leaders working together to redistribute access to wealth, help more founders succeed, and disrupt the venture capital ecosystem. Learn more at or by connecting with us on Twitter and LinkedIn.

The Next Decade Will Bring More Venture Capital To Female Founders

Emily Weiss - Founder, Glossier

This article by Geri Stengel was originally published on

The 2010s were a decade of slow progress in funding for female founders. However, the 2020s will see accelerated progress as investors see even more proof that investing in women brings stellar returns.

Continue reading here.

Operator Collective is a diverse group of leaders working together to redistribute access to wealth, help more founders succeed, and disrupt the venture capital ecosystem. Learn more at or by connecting with us on Twitter and LinkedIn.

What companies should strive for in a down market

Photo by Christopher Michael

The COVID-19 outbreak leaves today’s markets in flux, and naturally there are two general categories of thought when it comes to how venture capitalists will react. 1) Venture firms will sit out the next few months and not deploy capital as they focus on supporting their existing portfolio, or 2) Venture firms are open for business, knowing that incredible businesses were built during the last economic downcycle (aka: the 2008 financial crisis).

At Floodgate, our investment strategy remains largely unchanged. Our mission is to back founders who have the grit, vision, and courage to not only survive, but actually thrive in an economic environment where there are no guarantees the next funding round is right around the corner. Even over the last few years when it seemed that capital was aplenty and companies without a clear path to profitability were able to raise large rounds of funding, we’ve encouraged founders to be practitioners of Intelligent Growth. (So much so that we teach a class of the same name at Stanford!) 

What venture firms look for in down markets 

The premise of Intelligent Growth is that a startup needs to hack value before it hacks growth. That’s the key message here: Especially in a downturn, companies must be sure they’ve reached product-market fit before they prioritize growth. Does that feel counter-intuitive?

Over the past few years, when venture funding seemed abundant — more funds were popping up and existing firms were raising larger funds — companies and VCs alike were prioritizing growth, sometimes in the absence of a sound business model and often before product-market fit was clear. Companies started taking a “growth at all cost” approach to reaching triple-digit growth rates — even when the cost of acquiring customers continued to outpace the lifetime value of those customers, margins were deteriorating, or there were other signs that product-market fit had not been achieved.

In fairness to founders, they were often solving for what they thought would get their companies noticed and funded, so the ecosystem started to confuse high growth rates with evidence of product-market fit. But how is a founder to know if product-market fit has been achieved? There are many definitions of product-market fit, but they generally center around creating moments of delight for customers that are so compelling, that instead of the company pushing its products to customers, customers are pulling the products from the company.

“Growth at all costs” leads to fake progress

Unfortunately, what those concepts often fail to take into account, especially in the early days of a business, is whether the unit economics are (or will become) attractive and whether the company can ultimately grow in an efficient manner.

Take the example of an ecommerce company who uses free credits to get customers in the doors, only to have the customers churn once the credits expire because the service itself was not fundamentally valuable. The company may be able to use its own capital to, in effect, buy growth via net-new sign-ups, but without an ability to retain and monetize an active customer base, the growth is clearly not sustainable. So while the company may appear viable from the outside, the inflated growth rate creates an unstable foundation. It is, in effect, fake progress

Finding product-market fit in a down market 

A much more sane approach to building a company is to not only strive for product-market fit, but to also position yourself competitively in your ecosystem with a business model that can evolve to let you be self-sustaining someday — to control your own fate. This does not mean you need to monetize on day one, of course, but rather that you always maintain a sense of what you’re building toward and whether the ecosystem you play in (your customers, suppliers, partners, and competitors) will accommodate your business model. To learn more about how to solve for not just creating a Minimum Viable Product but becoming a Minimum Viable Company, even in the early days, read this blog post by Floodgate co-founder, Ann Miura Ko.

To be clear, growing intelligently does not run counter to growing quickly or blitzscaling. When does a start-up begin to Blitzscale? Entrepreneur Reid Hoffman like to say this happens when “you’ve ironed out the product-market fit, you have some data, and you know what the competitive landscape looks like.”  

Intelligence growth starts with creating value

There’s a time and a place to invest in scaling your company, but that time is not before you’ve attained product-market fit; growth alone is not evidence of that magical moment. Whether we’re in a bull or bear market, you want the fundamentals of your business to be sound so you’re not dependent upon a large next round of funding to buy you more time.

Stay calm and grow intelligently, my friends. 

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