He Was Crushing It at Cisco. Then He Left Everything to Build His Own Sales Machine.

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At just 24, Riley Reist was already closing $30 million in enterprise deals at Cisco. He was one of the top reps in the country,  and the youngest. On paper, he was winning.

But he didn’t feel like one.

He had done everything right: landed the prestigious job, hit the big numbers, fast-tracked his career. But something was missing. Riley didn’t want to spend his life selling someone else’s product, no matter how good he was at it.

So he left. Not to build a business right away, but to learn.

Over the next two years, he joined two VC-backed startups as their first sales hire. Both were early-stage. Both had zero revenue. And both taught him exactly what most technical founders struggle with: building a repeatable sales engine from scratch.

That’s when it clicked.

Most startups don’t need a VP of Sales. They need someone who can plug in fast, build momentum, and coach the founder to close.

So Riley launched his own agency, and  combining content, outbound, and founder sales coaching into one full-stack go-to-market system.

No fluff. Just pipeline, revenue, and results.

Now, less than two years later, he’s helped early-stage startups close over $10M in ARR,  all while staying lean, hands-on, and hyper-focused.

I sat down with Riley to unpack how he made it happen, and where he’s going next.

1. Who are you and what do you do?

 I’m Riley Reist, and I run a go-to-market agency based in New York City. We help early-stage startups, both bootstrapped and VC-backed, get from zero to their first few million in revenue.

Our focus is founder-led growth: we help founders build authority on LinkedIn, generate qualified leads with outbound campaigns, and actually close deals. I also personally coach founders through sales cycles,  and sometimes even jump on calls with them.

2. What’s your backstory? How did this all begin?

 I started out in competitive tennis, then moved into enterprise sales at Cisco. I had early success, $ 30M+ closed, top 3 rep nationally - but I felt stuck. I wanted the chaos and creativity of startups.

So I left to become the first sales hire at two VC-backed startups. Both were pre-revenue. Both had technical founders. And both taught me how insanely hard and fun early-stage sales is.

That’s when I realized: most founders don’t need a full-time head of sales. They need someone who can plug in fast, generate a signal, and get things moving. So I built an agency around that.

3. How did you land your first clients?

I messaged every founder and VC I knew in New York. Told them I was starting this thing, asked if they knew anyone who needed help.

I didn’t do any cold outbound for myself, which is ironic, because that’s what we do for clients. But my network responded. Four clients came in within the first month.

4. What’s the secret sauce? What do you actually do for clients?

Every engagement starts with LinkedIn content for the founder. We help them post high-quality content to build trust and awareness.

While that content runs, we build highly segmented outbound lists using tools like Clay. We run cold email and LinkedIn campaigns in parallel, and then build creative plays on top of that.

For example, we track everyone who likes or views the founder’s LinkedIn posts, enrich that data, and reach out with personalized emails. Or we’ll host Michelin Star dinners for ICPs in major cities. That campaign alone generated millions in pipeline.

Once leads come in, I coach the founders directly. I help them close deals, improve their pitch, and build repeatable sales motions. Sometimes I even join the calls myself.

5. How’s the business doing today?

We’ve helped early-stage startups close over $10 million in ARR.

Right now, we’re a lean team: one full-time in NYC, a few offshore contractors for data work, and myself. The big challenge now is scaling myself out of the business. I’m hiring, building systems, and slowly handing off execution so I can focus on strategy and growth.

6. Any big “oh shit” moments?

Not the usual kind. The main temptation has been offers,  every client wants me to join full-time. It’s flattering, but I built this because I want to work with multiple founders and own my time.

7. What’s the one thing outsiders don’t get about this work?

How powerful it is to combine content, outbound, and sales into one integrated system.

Most agencies only do one of those. But when you combine them, they feed into each other. Content helps you write better outbound. Outbound creates warmer leads. Sales calls give you new content ideas. It’s a flywheel.

We don’t just generate leads,  we build a system that founders can scale themselves.

8. Favorite tools?
Clay, N8N workflows, PhantomBuster, Triggerfy, Gmail + Superhuman, Notion, ClickUp, and Slack. ( hyperlinks )

Also: my brain. It still comes up with the best campaign ideas.

9. What’s next?
Scale the agency. Build a world-class team. Only work with startups and founders I’m genuinely excited about.

The agency is a cash engine and a relationship builder. Long term, I want to become an investor. This is step one.

Final Takeaways

1. Use your strengths early: Riley used his network to get early clients. He didn’t overthink it. He just shipped.
   

2. Build the flywheel: Content, outbound, and sales aren’t separate. When you treat them as one system, things compound fast.
   

3. Don’t sell your time forever: Even if you’re great at something, build systems. Delegate. Create leverage.
   

4. The right clients make all the difference: Riley doesn’t work with just anyone. The best work happens when values and goals align.