How to build and lead a world-class startup team

Break through bias in the recruitment process and other leadership lessons from PagerDuty, DocuSign, Jasper, Zapier, and Twitter.

This is Lesson 6 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.

Building a great team is an investment in your startup’s future. Even when leaders see and agree about its importance, hiring and other “people” priorities are often the first to get sidelined when other things feel more urgent. 

As a founder, recruiting talent and creating a great company culture will be a core part of your role — and the amount of time and resources you dedicate to it (or don’t) will serve as a model to the rest of your organization. 

Getting started can be daunting. To give you a jumping off point, we’re sharing a few leadership lessons from first-time and seasoned CEOs from PagerDuty, DocuSign, Jasper, Zapier, and Twitter, plus an inclusive leadership framework adopted by Procore. 

1. Break through bias in the recruitment process

When Jennifer Tejada joined PagerDuty as CEO in 2014, she set out to turn the company into a market leader and one of the world’s most diverse software companies. “Anyone should look at the leadership team and see themselves mirrored in some way,” Jennifer says. “Representation matters because it proves to everyone that there’s opportunity.”

The senior leadership team at PagerDuty is composed of 45% women and 38% people of color. In our interview Jennifer and former Head of Inclusion, Diversity, and Equity, Marcus Cooper (now a leader at Nike), share six steps the team took to address personal bias and structural inequities in the recruiting process that tend to keep marginalized groups out of senior roles.

  1. Prioritize team values over personal ego. Consider candidates who are humble, hungry, and have high emotional intelligence — these profiles often thrive in leadership roles.
  2. Use impact as a proxy for future success. To assess self-awareness ask candidates: “How did you know when you were making progress for the business and your team?”
  3. Design equitable interview questions. Create behavioral questions that pertain to your company values rather than relying on vague, biased “culture fit” assessments.  
  4. Build a bigger talent funnel. Hire recruiters who have diversity experience and training and can differentiate between a necessary skill for a role and something that can be coached. 
  5. Rely on data to measure progress. Track representation across identities and find a proxy to measure inclusion. Consider using a platform such as Hibob or Culture Amp to help.  
  6. Slow the search down, if necessary. Even if your company is scaling quickly, resist pressure to make a hire before interviewing a diverse slate of candidates for each role. 

In our interview, Jennifer and Marcus also share vital leadership practices that help generate regular and meaningful employee feedback, and keep diverse teams engaged. Keep reading

2. Consider an executive recruiter — it could be your highest ROI investment 

Growing up, the most successful entrepreneur Dave Rogenmoser knew of was a man who owned a few local Wendy’s franchises. This was enough to inspire Dave’s entrepreneurial itch. Later on, at a wedding, Dave met his future co-founder, and together they went on to start a company called Proof.

Proof didn’t perform the way Dave had hoped, but he was undeterred. The same year he sunsetted Proof, founded another startup, Jasper, to help marketers write content using AI. A mere 18 months later, Jasper became a unicorn. 

Much was unconventional about Jasper’s rapid, meteoric rise, including how they scaled the team. The first year, they intentionally chose not to hire anyone and used their limited resources extremely wisely. It saved them plenty of runway, but created challenges down the road. 

“It was probably unwise to go from nine to 180 in a year. We ended with great new people, but nobody knew what we were doing. Their boss joined a week before them, and their boss's boss joined a month before that.” 

But there was one decision from that period that Dave stands by: bringing on an executive recruiter. “We ended up hiring a president I never could have hired, or even talked to.” While it cost $150,000 (a staggering sum to Dave at the time), it paid off in ways he could never have anticipated. “The trickle-down effect of solid leadership has been huge.”

In our interview, Dave also discusses lessons learned building a startup that failed, and his deep conviction that AI will enhance — rather than upend — human ingenuity. Keep reading → 

3. Avoid the trap of transactional working relationships

Wade Foster and his co-founder decided to make Zapier a fully remote company from the beginning, an unusual decision back in 2011. While certainly better off than many other startups, this model didn’t completely protect the team from the chaos of the pandemic. 

On a personal level, employees experienced the loss of childcare, mental and physical health, hobbies, and routine. On a professional one, they no longer had the twice annual in-person retreats that they’d relied on to form deeper and more authentic connections with co-workers.

“When that disappeared, you really started to notice how transactional distributed work could feel. It's an email, a Slack, a quick Zoom — and it's right down to business. When you do that for a prolonged period of time, you start to notice things just don't click quite in the same way.” 

Wade was determined to rescue camaraderie at Zapier by creating spaces to talk about things other than work. “One simple thing we've started doing in our meetings is check-ins to make sure we understand how people are doing. It’s a reminder that we're working with other people who have rich and full lives, and those reminders help us treat each other as humans.”

In our interview, you’ll get other incisive, prescient perspectives on the future of work from CEOs Anjali Sud of Vimeo, and Christal Bemont of Talend. Keep reading → 

4. Be unambiguous with C-suite roles and expectations

A few decades before Dan Springer became the CEO of DocuSign, he considered the internet a passing fad. Lucky for him, it wasn’t. In his remarkable career, Dan led two software companies through successful IPOs, including one that he rescued from the brink of bankruptcy. 

Dan’s experience gave him unique insight into what it takes to build a high-functioning executive team. When growing businesses, Dan has noticed that founders stay so focused on finding the right people that they lose sight of the need to define clear roles and expectations.

“My best advice is to be unbelievably clear on the role you're bringing in and how it's going to change.” By the time CEOs start recruiting for a C-level executive, they should already know how this person will fit into the organizational chart and what they will be responsible for — otherwise, they will be set up for failure. 

Being candid about the long and short-term vision for each role reduces conflict down the road. “Whatever you do, don’t leave it ambiguous. Most of the issues I see are caused when people are too polite to bring it up and be explicit about the nitty gritty. But this will kill you.” 

In our interview, Dan also discusses why he considers the pre-IPO period a good time to take big bets, and how his decision to become a stay-at-home dad impacted parental leave at DocuSign. Keep reading → 

5. Evolve your leadership to meet the needs of your startup

Bessemer Partner Sameer Dholakia was the CEO of SendGrid from 2014 to 2020, and he often jokes that, during this period, his job changed every year. To fulfill his new responsibilities and remain effective in his role as the company grew, he had to adapt his leadership approach. 

“In the early days of a startup, it’s natural to lead by example. It’s likely you’ll personally interact with most of your employees on any given day, so they can observe how you think, how you problem-solve, and how you embody your company’s values.”

But once your company grows too large for you to interact with most of your employees regularly, CEOs need a new approach. Sameer calls it leading through other leaders. While you’ll continue to set direction, it’s your executives who will be actually guiding each of their teams to the next destination. 

Eventually, you may reach a point where not even your executives are able to have close relationships with every person within their organization. When this happens, Sameer finds the most efficient route to reach all employees is to lead through ideas. 

“It's one thing to simply tell employees what the company’s values are, but it’s another to communicate an idea through a story. By sharing meaningful concepts via stories, you’ll allow your employees to make decisions that support your vision without needing to be in the room.”

In his article, Sameer shares other important lessons for your startup’s ‘teenage years’ — from preparing for maintaining fast-paced decision-making to developing your communication rhythm. Keep reading → 

Bonus exercise

Read our interview with diversity, inclusion, and equity expert Valerie Jackson, and her starter guide to building inclusive companies. If your startup has an existing team, consider using her workshop as inspiration for your own team-building session. If you’re in the very early stages of company-building, use the EACH framework to assess your existing inclusive leadership skills and where you’d like to invest in your own development.

This is Lesson 6 from Bessemer's How to Lead: Founders Fundamentals Course. Sign up today for mentorship from 30+ leaders.