We sat down with Sheri Flood because she knows what it takes to build high-performing sales teams with a strong culture. Sheri joined Middesk just over a year ago and today leads our entire Account Executive team. With more than 15 years of experience across SaaS, legal tech, and financial services — including leadership roles at Litify, Salesforce, and Daktronics — she brings a rare blend of enterprise sales expertise and early-stage team building.
Sheri is known for balancing performance with empathy, and she’s passionate about helping both customers and teammates succeed. In this conversation, she shares her approach to leadership, what excites her about Middesk’s growth stage, and her advice for anyone considering joining the team.
Why Middesk? And why the opportunity to grow and lead sales here?
“The mission stood out immediately. We’re helping businesses establish trust and reduce friction in one of their most critical moments: customer onboarding. That problem is both meaningful and urgent.
I was also excited by the stage of the company. We already have strong customers and early signs of success, but there’s still so much more to build — whether that’s product, process, or how we show up in the market. I’ve been at this stage before, and I really enjoy the mix of momentum and whitespace. And finally, the people sealed the deal. Everyone here is deeply committed to the mission and vision, and they challenge one another in a positive way that helps the whole team grow.”
What’s the mark your leadership style leaves on a team?
“I’d describe it as collaborative and supportive, with a focus on clarity. People should always know what we’re working toward and what ‘good’ looks like.
I also prioritize autonomy. AEs grow faster when they’re trusted to make decisions, test their instincts, and learn by doing. I’ve been an AE myself for many years, so I know how tough and rewarding the role can be. Empathy and authenticity matter — I strive to show up consistently every day, and I want my team to feel that. We win together, and we lose together.”
Looking back on your career in sales, what’s the insight that continues to guide how you coach?
“The biggest lesson is to assume nothing and ask everything. In every industry and customer conversation, curiosity is the difference between good outcomes and great outcomes. Discovery isn’t a one-time step; it’s an ongoing process.
That lesson shows up when I interview candidates too. I listen for how curious they are, what questions they ask, how they navigate ambiguity, how they learn in real time. Those instincts are what make a great seller.
But curiosity alone isn’t enough. The best AEs also bring a strong sense of ownership. Enterprise sales is complex and often ambiguous, and success requires taking full accountability — for your pipeline, your customers, and your own growth.
When AEs pair curiosity with ownership, they don’t just chase deals; they drive outcomes and help shape the culture of excellence we’re building at Middesk.”
Of Middesk’s values — lead with curiosity, embrace ambition, win together, put customers first — which do you find yourself living out the most?
“All of them matter, but if I had to choose one, it would be putting customers first. Everything we build and every decision we make should ultimately benefit our customers. Winning together is close behind. No deal happens in isolation. And of course, curiosity fuels everything: asking questions, uncovering needs, and building trust.”
Sales is a high-energy game. What’s your go-to way to reset outside of work?
“Family is number one. I have three young kids, and time with them is both grounding and energizing. It’s a daily reminder of why I do this work.
Beyond that, I try to maintain a consistent exercise routine, usually with a buddy so I also get the social aspect. A few workouts a week before the day starts makes a huge difference in my mindset. And when time allows, I like to pick up recreational sports. I started golf lessons last year and hope to add tennis next. Having something outside of work to improve keeps me balanced.”
What’s one influence — a read, a listen, or a ritual — that’s changed how you think about business?
“A book that’s had an impact on me is Extreme Ownership by Jocko Willink and Leif Babin. The core idea is that leaders must take full accountability — for outcomes, for decisions, and for their teams. That mindset has really shaped how I think about building a sales culture. In enterprise sales, things are complex and rarely linear; ownership is what allows teams to navigate ambiguity and still deliver results.
I also enjoy listening to podcasts like Masters of Scale and SaaStr. They’re constant reminders that the challenges we face in scaling a sales organization aren’t unique, and I find it energizing to learn how other leaders and companies approach them.
Finally, one habit that’s been transformative for me is daily reflection. Even spending ten minutes at the end of the day to process what went well, what could have gone better, and how I showed up for the team keeps me grounded and intentional. Over time, those small reflections add up to real growth.”
What excites you most about fueling Middesk’s growth through sales?
“We have a chance to redefine how businesses establish trust at scale. Middesk is uniquely positioned to solve problems that many companies are still wrestling with, and that’s a huge opportunity.
For the sales team, that means showing up as market educators, building long-term partnerships, and serving as the voice of the customer inside our walls. It’s not just about closing deals, it’s about shaping how businesses operate in the future.”
What’s the one thing you’d share with someone thinking about jumping into sales at Middesk?
“I’d say: come ready to be curious, ambitious, and collaborative. This is a place where you’ll be challenged with complex problems, but also supported by teammates who want to see you win. If you’re excited by the idea of building something meaningful, contributing to a strong culture, and making a real impact on how businesses build trust, then Middesk is the place for you.”
Sheri’s sales team is growing — want in?
If closing deals is your craft, come write the next chapter with us. Explore open roles at Middesk Careers.
