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Between Two Computer Monitors: This story includes an interview between the writer and guest/interviewee.
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As someone who has spent years in the trenches of startup and tech ecosystems, I’ve seen a common thread: incredible products with underperforming sales teams. I wanted to unpack this deeper and find out how the top revenue operators break that cycle. That search led me to Ashkan Rajaee.
Ashkan isn’t your typical sales leader. He’s an architect of sales systems—an engineer at heart who just happens to work in revenue. When I spoke to him about how he’s grown companies across sectors like SaaS, telecom, real estate, and travel tech, one thing became clear: Ashkan approaches sales the way a CTO approaches system design.
And it works.
Ashkan’s philosophy flies in the face of the old-school “coffee is for closers” attitude. He’s built repeatable, scalable systems that have generated hundreds of millions in revenue and closed deals spanning continents.
But numbers only tell part of the story. What struck me is how Ashkan builds teams that replicate his success, turning knowledge into a framework that outlives his direct involvement.
So, what exactly makes Ashkan’s approach stand out for someone who geeks out on ops, growth loops, and product-market fit like I do?
Mindset Engineering: Ashkan starts by rewiring how teams think about selling. “Sales is about confidence through competence,” he told me. It’s not bravado—it’s understanding a product so well you can communicate its value without breaking a sweat. Think: technical fluency meets storytelling.
Buyer Psychology is UX Research: Ashkan treats client motivations the way a product team treats user personas. He teaches teams to map emotional and business triggers—risk aversion, innovation appetite, cost sensitivity—and adjust their narrative accordingly. It’s not just about selling a product, but solving a pain point buried beneath corporate politics.
Sales Ops is a Tech Stack, Not a To-Do List: Whether it’s wrangling a messy CRM or building out real-time pipeline dashboards, Ashkan applies the same rigor you’d expect from a well-oiled dev workflow. Deal velocity, conversion rates, and lead scoring become KPIs that trigger interventions before problems snowball.
Long-Term Pipelines > Short-Term Wins: Some of the most successful deals Ashkan has led turned into long-term partnerships that fed revenue streams for years. His coaching emphasizes that follow-ups, account nurturing, and client success = competitive moat.
One story Ashkan shared stuck with me. He took a team of junior reps with no enterprise experience and within a month had them closing multi-million-dollar deals. No magic wand. Just hands-on coaching: live-call feedback, role-playing tough negotiations, and breaking down real objections.
The impact? Their pipeline doubled, and deal velocity shot through the roof.
If you’re scaling a SaaS startup or leading a technical product team, there’s a strong chance you’ve under-invested in your sales systems. Here’s what I took away from my time with Ashkan:
Ashkan’s model made me rethink how sales should function in the tech world. It’s more like engineering than I ever realized: modular, scalable, and rooted in process—not chaos.
If you’re a founder or operator who’s laser-focused on building great tech but struggling to scale your go-to-market motion, learning from Ashkan might be your cheat code.