# Profile: Ryan Reynolds and Owning the Outcome

[Eric Esten, Director of Revenue Strategy & Operations](https://www.clipboardworks.com/resources/blog/author/eric-esten)

January 22, 2026 8 min read

**Hi Ryan! Tell us about how you came to Clipboard**  
Before Clipboard, I worked on my own company that I started toward the end of college. It was an AI powered marketing company that automatically customized social media posts, marketing content, and email campaigns using customers’ existing blogs and materials. I built an early AI prototype, we had an MVP, and I spent about a year on it. That was my last year of college and my first year post-grad.

I then went through an NYU startup accelerator program and we were considering Techstars, but ultimately realized we didn’t have the product market fit we thought we did. What customers said they wanted didn’t actually line up with how they used marketing tools in practice.

Rather than forcing a pivot, I decided it made more sense to look for another role. I still wanted high ownership and autonomy, but I wanted something more stable than an early stage startup. That’s when I found Clipboard. It stood out as a role with real ownership and independence, but also the resources and connections of a larger company.

**How did you find the application process?**  
I really enjoyed it. After filling out a lot of applications and going through fairly generic interview processes, this felt like a breath of fresh air. Working on a real case helped me realize it was a strong fit, because the problems were genuinely interesting and aligned with what I like to work on.

The pricing case in particular stood out since it had more variables and nuance than most interview questions I’d seen. It felt like working on an actual business problem rather than an abstract exercise.

**Any tips for people applying?**  
My biggest tip is to dig deeper than the obvious answer. Don’t stop at surface level solutions. If something looks like the right answer, push one layer deeper and try to identify the root cause.

Surface level fixes often don’t work long term because the underlying issue still exists and will show up again in a different way. That root cause mindset is something we use a lot at Clipboard, and it’s applicable across cases and problems.

**What do you do now at Clipboard?**  
I run our inbound sales motion. I own execution on inbound deals end to end, making sure we reach leads quickly, distribute them logically and equitably across the sales team, and deliver a great customer experience throughout the pipeline.

That includes building and maintaining the systems that ensure inbound leads are handled consistently and effectively from the moment they come in.

Inbound represents a significant percentage of new demand today. From a growth perspective, that makes it one of the most critical functions in the company.

We’re a high growth company, and if inbound doesn’t work, we can’t grow to our full potential. Ultimately, everything else the organization does, from product to operations to marketing, depends on revenue and so nailing inbound is one of the most important things we can do.

**How has your role evolved since joining Clipboard?**  
I started as a Market Owner in Boston. In this role, I was tasked with growing both sides of the marketplace (facilities and professionals). I later focused on the demand side, specifically in the Boston area, where I focused on selling to facilities in person, and getting them to switch over from our competitors. Eventually, I completely moved into the sales org and worked on enablement initiatives like building a Corporate Customer Dashboard within the application.

I now lead inbound sales. My focus is pushing on our system so we can get to customers faster and give them the best possible experience when signing up for the platform. This work ensures that when a facility is ready to sign up, they spend less time waiting and have fewer steps to complete, because we keep the process simple and easy on their end. In practice, this means building a tight partnership with our AE team, auditing execution quality, creating automations that speed up key steps, and collaborating across the organization to leverage tools other teams already use that can also support sales.

**What do you like most about working at Clipboard?**  
What I like most about working at Clipboard is how scrappy we can be.

Even though the company is large, the day to day feels like a team that’s always hungry. If you have a clear problem, a strong hypothesis, and a way to measure impact, you can move fast. I don’t feel stuck behind layers of approvals. There’s a real bias towards action. We are constantly shipping something, learning from real outcomes, and iterating.

I also love that the teams aren’t siloed. A lot of my work sits at the intersection of sales, product, ops, data, and GTM. It’s normal to jump into a problem with cross-functional partners. That’s energizing because it means I can work on projects I actually care about, not just tasks assigned inside a narrow role.

The other piece is how close we stay to customers and the real world. Clipboard’s product isn’t abstract. When we improve a workflow, pricing, onboarding, or reliability, it shows up in the customer experience. That direct line from effort to outcome is motivating, and it makes the work feel high leverage.

Finally, it’s a great environment if you like learning by doing. I’m naturally data driven and love digging into what’s happening, why it’s happening, and what lever to pull next. Clipboard rewards that mindset: bring the data, talk to users, propose a change, test it, and own the result.

**What’s your proudest achievement so far?**  
My proudest achievement so far is improving inbound response time efficiency and coverage across nights and weekends.

When I started looking at it, it wasn’t just a “people working hard” problem—it was a systems problem. Coverage and handoffs were inconsistent, the same edge cases kept popping up, and it was too easy for leads to slip through the cracks after hours. I focused on making the work easier to execute correctly every time: clearer routing and escalation paths, tighter expectations for who owns what and when, and a more consistent way to surface what needs attention.

A big part of what made it rewarding was building a setup that didn’t rely on heroics. Instead of relying on individual knowledge or memory, we put repeatable structure around it: lightweight workflows, visibility into what’s happening in real time, and simple checks that made it obvious when something was stuck. We also defined what “good” looks like and tracked it so we could tell if changes were actually working, not just feeling busy.

The outcome I’m most proud of is that it improved both speed and consistency across all hours of the week. It made nights and weekends feel more predictable for the team, and it raised the floor on execution so customers got a better experience even outside normal business hours. Building something durable, where performance holds up even when things get chaotic, has been the most satisfying part.

**Tell me about the “Gritty” award**  
We created “Gritty Inbound of the Week,” a team ritual to celebrate someone who handled a tough inbound situation exceptionally well. It’s not about being flashy; it’s about recognizing the kind of effort that actually moves the work forward.

What makes it fun is the energy around it. We elect a winner, recap what happened, and the winner gets a little moment of spotlight that feels earned. Over time it’s become a positive feedback loop: people learn from the best plays, inside jokes develop, and the team gets a regular reminder that the hard parts of the job are also the parts we’re proud of.

It sounds small, but it’s been one of those simple rituals that builds culture. We celebrate grit, build camaraderie, and make the work feel lighter without taking it less seriously.

**What do you like to do outside of work?**  
I snowboard, play adult flag football, and follow Boston sports.

**What position do you play in flag football?**  
I’m defense first. I play middle of the field safety or linebacker.

**Who’s your NFL comp?**  
Patrick Willis.