CEO Rapidfire: Scribe CEO Jennifer Smith On The Hidden Power Of Making Tradeoffs

Welcome to CEO Rapidfire, fast-paced questions with today’s most successful founders and CEOs. Be sure to look for these special Q&A editions of my newsletter, where I’ll share insights from the amazing leaders in my network.

My newest guest is Jennifer Smith, co-founder and CEO of productivity software company Scribe, who’s fine with doing things the hard way. (For more, keep reading!)

Scribe’s Workflow AI platform helps organizations take the manual toil out of documenting and scaling how work gets done. Rather than copy-and-pasting screenshots or recording videos, you can instantly transform any workflow process into an elegant step-by-step guide and share it with your team. Scribe, whose customers range from early-stage startups to almost 95% of the Fortune 500, recently topped four million users. So far, the company has raised more than $50 million, including a $25 million Series B round last year.

Jennifer, who was born in upstate New York, has a degree in economics and finance from Princeton and an MBA from Harvard Business School. After interning at Lehman Brothers, she spent seven years with McKinsey & Co., where she led a team focused on serving clients in technology and financial services. In the management consulting world, she saw how cumbersome and inefficient it was to document and share workflows — a challenge that became the spark for Scribe. Jennifer then worked in business development at venture capital firm Greylock Partners, whose investments include Airbnb, Facebook and my first company, AppDynamics. She launched Scribe in 2019 with Aaron Podolny.

Jennifer, who likes to bake chocolate-chip cookies by night, considers herself an accidental entrepreneur. “If you had asked me even a few years ago before I started Scribe, I would have said no, likely not,” she says. “To me, I fell in love with a problem.”

If it feels hard and you constantly feel like you’re making trade-offs, you’re probably doing it right. 

Here’s what Jennifer shared in our CEO Rapidfire interview:

The one secret to succeeding as a leader, in 5 words or less. Know thyself, and adjust accordingly.

What was the most exciting “minute” of your leadership journey? Our first credit card swipe from our first paying self-serve user (halfway across the world). 

One truth you wish you knew about leadership before starting? If it feels hard and you constantly feel like you’re making trade-offs, you’re probably doing it right. 

If you had to do battle with a giant, what weapon would you use? Slingshot. With laser focus, even small efforts have big impact. 

Your worst mistake as a leader (and what you learned from it): Making decisions based on how strongly people feel vs. what I know to be correct. I’ve learned to drown out noise and look inward to my gut instead. 

Create a shared definition of winning. Make the team’s win each person’s win, and vice versa. 

Top 3 websites, blogs or podcasts you can’t imagine your day without: I consume remarkably little news media. I learn mostly from long-form conversations.

What popular leadership advice do you disagree with? Servant leadership. Serving the mission and customers might make some people uncomfortable, and that’s OK. [Also] that formal schooling is valuable for career progression.

One life hack you can’t live without: Am I allowed to say Scribe? 😛

One soft skill that you’ve realized is supremely important: Ruthless prioritization. Become truly excellent at a few things vs. good enough at many.

The one thing that makes a good leader great is: Self-awareness.

Your secret to building a great team is: Create a shared definition of winning. Make the team’s win each person’s win, and vice versa. 

The key to navigating hypergrowth is: Operating as close to the edge without falling off.

Every leader must read … High Output Management by Andy Grove. Old, but good. I quote it to my managers a lot. 

What are you most excited about at work right now? AI and the opportunity to transform how people work.

Your one “non-negotiable” in business (or life) is … Optimize for sleep. You can’t be your best (or anywhere close to it) otherwise.

Thank you, Jennifer, for sharing your leadership thoughts this week. To learn more, follow Jennifer on LinkedIn.

Thank you for reading! I'm interested in hearing your thoughts in the comments below. For more insights from my experience as a serial entrepreneur and how we can harness the power of software to change the world, be sure to subscribe to Entrepreneurship and Leadership.