From College Dropout to Building a $12M Agency (Connor Jeffers’ Story)

TLDR: The platform bet that built a $12M agency

Connor Jeffers traded a MacBook Air offer for a college dropout decision that led to building Aptitude Eight, a $12M HubSpot agency he later exited. His path from Salesforce RevOps specialist to HubSpot ecosystem leader reveals how early platform adoption creates competitive moats before markets saturate.

Listen to this episode to learn why LinkedIn generated 100% of leads for three years, how entity separation enabled HubSpot Ventures investment, and the focus lesson that Connor calls his biggest regret.

Meet the guest: Connor Jeffers, founder of Aptitude Eight

Connor Jeffers built Aptitude 8 from zero to $12M in revenue by betting early on HubSpot's emergence as a Salesforce competitor. Before founding the agency, he worked at TopHat where he became the internal RevOps expert, then consulted for early-stage startups at a venture studio.

Connor's journey from college dropout to successful exit demonstrates how platform ecosystem expertise compounds when paired with consistent thought leadership. He now focuses on Happily, a software business building high-value HubSpot apps after learning that marketplace discoverability requires direct sales investment rather than organic discovery.

Chapters

[00:32] Connor's MacBook Air offer: the summer internship that replaced college

[04:22] How TopHat's growth from 50 to 200 people created a RevOps generalist

[10:08] The HubSpot thesis: why Connor bet against Salesforce ecosystem saturation

[14:29] Three years of 100% LinkedIn-sourced leads before channel saturation

[19:24] Four business phases: discovery, engineering, scale, and execution

[26:15] The Dax acquisition and App Chemist integration into Aptitude Eight Labs

[33:34] Why HubSpot Ventures required separate entities for investment

[37:46] Zebra's retention disaster: when sales success masks product-market fit problems

[44:40] The focus decision Connor calls his biggest regret

[47:57] "Do good work and the rest will follow": advice from a childhood mentor

Key Insights

SaaS teams debating internal development versus hiring specialists can learn from Connor's cross-functional path at a scaling company.

Connor's TopHat journey started with a simple incentive. "He was like, if you do this, we'll get you a MacBook Air. And I was like, oh, that'd be pretty sick," he explains. That summer role evolved into moving to Canada, joining marketing, and scaling with the company from 50 to 200 people while gaining experience across marketing, RevOps, and Salesforce implementation.

For growth leaders managing coordination overhead, early operational experience at scaling companies creates versatile team members who understand allbound coordination naturally.

SaaS growth leaders facing channel saturation can study how early platform adoption creates sustainable competitive advantages.

Aptitude Eight generated 100% of leads through LinkedIn for three years through timing and genuine expertise. "LinkedIn now is pretty saturated. It's still a great channel. Yeah, we were early," Connor notes. Their strategy involved publishing technical content about HubSpot's emerging features like custom objects and coded actions before the platform became crowded.

The key is establishing authority through valuable content that demonstrates real expertise rather than surface-level marketing messages.

SaaS teams can sustain LinkedIn performance even in saturated markets by prioritizing authentic engagement over volume.

As we discuss in the episode, Connor's LinkedIn success mirrors what we've learned at Understory. Our content strategy involves posting about tactics we're actually doing for clients and internally, not being overly promotional. Strong branding and low-friction contact methods allow the work to speak for itself.

We maintain weekly goals for meaningful LinkedIn comments rather than generic responses. The philosophy: like every comment to show appreciation, but leave AI-generated comments blank to signal we recognize low-quality automated engagement.

SaaS companies struggling with expansion timing can follow Connor's adjacent opportunity approach rather than dramatic pivots.

Each of Connor's transitions built on previous expertise while expanding into related markets. Starting as TopHat's Salesforce expert, he later recognized HubSpot's emergence as an opportunity gap. "My thesis was basically like, this seems really interesting and there's an opportunity here. And if these guys are actually going after Salesforce, like there could be something there," Connor explains.

Successful expansion leverages existing strengths in new but related markets rather than chasing unrelated trends.

Agency work creates a natural path to SaaS by revealing product gaps that clients experience daily.

As we discuss in the episode, Connor's agency-to-software journey resonates with conversations Ali and Alex have daily at Understory. When doing agency work, it's a natural evolution to move into SaaS because you play with so many different products, learn where gaps are, and learn how to plug those holes.

Connor lived this pattern: his services expertise revealed HubSpot ecosystem gaps that became Happily's product roadmap.

SaaS leaders often waste resources by applying the wrong tactics for their business phase.

Connor breaks down business development into distinct phases: discovery, engineering, scaling, and execution. Aptitude Eight reached the execution phase where "you get more value out of incremental improvements and shaving efficiency and doing a lot of these pieces than you do out of making something new."

Understanding which phase your business occupies determines whether you need experimentation, product development, systematic scaling, or operational optimization.

SaaS leaders managing services and software face partnership conflicts that proper entity separation solves.

When Connor structured the software business, he deliberately kept it as a separate C-Corp from his LLC-based services business. "I did that intentionally at the outset because I didn't want the software IP to pull into the services business," he explains.

This proved crucial when HubSpot Ventures wanted to invest but couldn't invest in a partner. "I was like, actually, we already solved that problem for you." Proper entity separation allows specialized optimization while preventing conflicts that limit strategic opportunities.

Platform ecosystem bets require realistic assessment of how users actually discover solutions.

Connor's experience building HubSpot apps reveals why marketplace assumptions often fail. "There is no discoverability in the HubSpot app ecosystem even today. If you build it, they will not come," he notes.

SaaS growth leaders considering platform plays must evaluate actual user discovery behavior. Success requires either high-value products justifying direct sales or significant paid media investment to drive discovery.

SaaS teams misunderstand channel attribution by tracking direct responses instead of influenced pipeline.

Connor's discovery challenges connect to a broader attribution problem we see constantly. As we discuss in the episode, people misunderstand outbound in critical ways: they only track direct responses instead of influenced pipeline. Two thousand emails might get 20 direct replies, but that ignores people who visit the website then convert via retargeting.

Thinking about channels in silos, whether outbound email or marketplace apps, misses how touchpoints work together to drive conversions.

Product-market fit validation must include implementation and retention reality checks, not just sales success.

Connor's Zebra product taught him that strong sales can mask fundamental viability issues. "Great product to sell, did really well initially, horrible to retain and implement because everybody's backend financial infrastructure is like a disaster," he explains.

Each customer required custom work to clean up payment data and reporting needs. Products requiring extensive customization indicate service opportunities rather than scalable software businesses.

Focus creates compounding returns that divided attention cannot match.

Connor's biggest regret involves splitting attention across multiple businesses. "Focus is a superpower and trying to do a lot of things at the same time is a really bad way to achieve results," he reflects.

His co-founder Dax noted that after concentrating solely on events, "I've never worked on anything where my work has compounded year over year before as hard as this." Energy compounds when consistently applied to a single focus area.

"Do good work and the rest will follow" beats outcome-focused thinking for sustainable success.

Connor's childhood mentor shaped his approach with advice focused on craft excellence. "If you focus on how I can do really great work and how I can make the thing that I'm doing really good, all the upside just comes naturally," Connor explains.

This philosophy prevents short-term thinking from exit calculations. Sustainable success comes from loving the process of building valuable solutions rather than working backward from desired outcomes.

Want more insights on platform strategy and SaaS scaling? Listen to the full episode on YouTube and subscribe to Understory's podcast for more conversations with SaaS growth leaders.

Looking to coordinate your paid media and GTM engineering without specialist management overhead? Book a call with Understory to explore how expert allbound execution eliminates vendor coordination and lets you focus on strategic growth decisions.