Founding GTM Spotlight: Jared Gaynes

In our founding GTM series, we give a voice to early-stage operators building their company's Go-to-Market motion.

We sat down with Jared, who was the founding GTM hire at Thena, a modern B2B ticketing system taking on incumbents like Zendesk and competing with start-ups like Pylon. His journey from data analyst to early stage sales served as the inspiration for exploring his own venture.

Julian: Before getting into sales you started in a data analyst role where you had to use SQL and other analytics tools. How did this technical foundation help you be a better AE?

Jared: This was an intentional yet unconventional decision. Coming out of college with several BDR offers, I chose an analyst role instead. My logic: learning how software works at the foundational level would serve me better as a seller. Instead of memorizing talk tracks, I could speak from actual experience with the product.

When you've only worked in sales, it's surprisingly difficult to understand how other organizations operate. My customer success experience gave me insight into what CS teams prioritize - knowledge that proved invaluable when selling to CS teams at Thena.

It's obvious when selling a technical product if you know what you're talking about. Without technical exposure - either through a coding bootcamp like General Assembly or working in a technical role - you'll struggle to truly empathize with prospects.

Julian: What drew you to work with Mike Molinet at Thena as Founding GTM hire? How did the experience shape your PoV on GTM strategy?

Jared: When you listen to successful entrepreneurs, there's almost always an inflection point where they found a strong mentor. I knew I wanted to start my own business someday, so I needed to work for someone who had successfully built a company.

Two things specifically drew me to Mike. First, he was a second-time founder, having built Branch into a unicorn after literally sleeping in a garage and showering at gyms. I had other offers but knew that Mike’s mentorship would be something special that’d likely be impossible to find anywhere else. Second, I saw a LinkedIn post where Mike emphasized always doing the right thing in business, even when it causes friction. This resonated deeply after talking to many sales leaders who seemed to care more about the deal than the truth.

Working for Mike taught me lessons I didn't have to learn through my own failures - insights that would later shape my own approach to building.

Julian: In the 0-to-1 phase, what is the most important thing you can do as an early GTM hire?

Jared: Relationships. Most people think early GTM is about the product, but the reality is the product always sucks at this stage. You're selling your own credibility, knowledge, and services on top of a basic, buggy product.

My priorities became:

1. Building relationships

2. Promising value they'll achieve by working with you

3. Creative differentiation

4. The actual product (surprisingly last!)

Being creative is essential when asking someone to bet on you instead of an industry standard.

Story 1: I was in a head-to-head deal with our first potential publicly-traded customer and needed to tip the deal in our favor. The Head of CS was a big Chiefs fan, had just been promoted, and the Chiefs had just made the Super Bowl. Instead of sending a cake, I commissioned a Cameo from “Fake Andy Reid“ congratulating her with a very personal note about her promotion and the Chiefs. She shared it with her entire team, instantly boosting Thena's visibility (GTMBA note: in December, we wrote about a deal I lost where my competitor did something very similar).

Story 2: One story that inspired me is that of start-up Friend, where the founder used his entire $1.8M seed round to buy the domain www.friend.com. Ridiculed by his peers at first, the move turned out to be genius and drove millions of visitors to his website.

Julian: You described Mike as someone who was a stickler for “doing things that don't scale.” Can you share an example?

Jared: When I wanted to automate our contract and billing process, Mike immediately shot it down. His reasoning? We'd inevitably change our pricing model - and he was right. We changed pricing six times after that conversation! If I had built that automation, I would have rebuilt it six times.

The lesson: automations at the seed stage remove the personal touch that's critical and actually slow you down. Mike insisted, “Don't automate emails when someone books a demo. Personally welcome every prospect.”

Many founders raise their seed round and immediately buy tools before establishing the correct playbook. Mike's approach was to do things manually first, learn what works, then automate once you have a proven process.

Julian: What are your top 2 hacks to land your first sales job?

Jared: First, act like a BDR. Create a list of 100+ potential companies using tools like Clay or industry news sources like BuiltIn to find promising startups. Analyze each company's health using Crunchbase and LinkedIn. A quick indicator: check if headcount is increasing or dropping in the LinkedIn “Insights” section.

Second, use Layoffs.fyi to identify companies with recent layoffs. This shows which organizations might be struggling and which are stable. Once you've identified promising companies, find three people at each doing what you want to do, and reach out with a personalized message - just like effective sales outreach.

Julian: Your LinkedIn says “Building Stealth”. What's next?

Jared: While leading sales at Thena, I encountered numerous challenges around customer-facing functions. I've been developing a side project leveraging AI to address these gaps.

At Thena, we grew from a handful of design partners to over 100 customers. Witnessing this journey from validated idea to first $1M in revenue gave me confidence that I could build something myself. Similar to my former colleague Brendan, who's now building Volca, I'm taking what I learned from Mike and applying it to my own venture. Stay tuned!