Employee Spotlight - Holly Anfinson, Enterprise Account Executive

By
Holly Anfinson
May 30, 2025
min read
Updated
June 16, 2025
Photo credit
What It's Really Like to Sell at Scribe


5

1. Let’s start with your story. What’s your background in sales?
What a perfect moment to reflect since I'm coming up on 10 years as a SaaS seller. It’s been quite the journey.

I got my start at Tableau in a commercial sales role, taking a leap into software sales with zero experience. That “yes” turned out to be one of the best decisions of my career.

Since then, I’ve had the chance to work at some incredible companies — including Box, Twilio Segment, Miro — spanning different stages, products, and customers. I’ve sold to everyone from scrappy startups to Fortune 500 giants, in both new business and account management roles. That variety has kept me sharp and curious.

More than anything, I’ve been lucky enough to learn from the best: world-class teams, leaders who push you to grow, and customers solving real problems. Each chapter has made me a better seller, and I couldn’t be more excited to kick off the next decade of my sales career with Scribe.


2. Why did you choose to come work at Scribe?

I’ve always sought variety in my roles, but when choosing a company, I focus on three key things: people and culture, product, and market opportunity. Scribe nailed all three, and then some.

From my first interviews, I could tell this team was special. Every person I spoke with had genuine excitement for the product and our customers, and that kind of energy is highly contagious. It's exactly the kind of team I want to hustle with!

The product fit and market opportunity were also undeniable. The volume of inbound interest and the customer love I saw in my research (check out scribehow.com/reviews) made it clear just how well Scribe is solving a big, universal problem in a purposeful way.

But what really sealed the deal was my final conversation with Jennifer, our CEO. Hearing her vision and values made it crystal clear: Scribe is building something meaningful, generational, and bigger than all of us. That clicked for me, and I knew I wanted in.

3. What have your first few months at Scribe been like?

Fast! And in the best way. At Scribe, we're encouraged to learn the basics quickly and then dive right in. I was leading customer calls by week two, with tons of room to learn through doing, and fine-tune along the way.

What’s really stood out is the strong culture of coaching and collaboration. There’s constant brainstorming on how to approach different customer scenarios, and it’s clear everyone wants to see each other succeed.

Almost a quarter in, I’m amazed at how much I’ve already done. The pace is energizing, the learning is real-time, and the support is unmatched. It’s felt different (better) than any role I've had before.

4. Scribe’s sales team in an emoji, go!

I had to choose two.

Every single person on Scribe’s sales team will hold a ladder for you so you can reach greater heights. There is no gatekeeping here. Everyone wants to see you succeed, and that kind of energy is contagious.


The sales team works hard and is also fun and lighthearted. The conversations in our Slack channels make me laugh out loud on the daily. I appreciate the levity! 

5. What’s your favorite feature or workflow in Scribe, and how do you explain it to customers?

Guide Me makes our users superheroes! 

Prospects often come in knowing Scribe can take the pain out of creating and documentation, but when they see Guide Me in action, that’s when the lightbulb really goes off. It’s the moment they start picturing how it will transform the way their teams work. 

I usually frame it by highlighting a common pain point: how hard it is for employees to find and follow workflows, especially when nothing’s documented or standardized? Then I show how Guide Me guides them through a workflow without having to dig around, context switch, or stop doing their work to learn how to do this new thing.

I hear a lot of “wow” or “this is a game-changer” from my customers. Guide Me doesn’t just make documentation easier (although it does completely automate that) — it also reshapes how knowledge flows through the organization, breaking down siloes and helping teams work smarter and faster.

6. What’s one trait that helps you succeed in sales, and how does it show up in your work?
Being a connector! When it comes to working large deals, there are a lot of complex requirements and moving parts. My strength is in mapping out and organizing the steps we need to take during an evaluation, connecting the right people (on my side across marketing, product, and customer success; and on the customer’s side). When everyone is clear on context, timing, and their roles,  the evaluation feels great for everyone. This requires a lot of teamwork and planning. It can often feel like putting together a puzzle, which for me is the fun part. 

7. What advice would you give to someone considering a move to Scribe or an early-stage startup in general?
Embrace the unknown. You’re not going to have all the answers or know how to navigate every call or situation. Don’t let that hold you back from diving in, because that’s where the growth happens.

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