Author profile

OlegBolotnov

Founder & CEO of PitchMonster. Selling since 15, from Kyiv subway kiosks to SaaS partnerships. He writes about the part of sales training everyone skips: practice.

15Age he sold his first Vodafone plan, in the Kyiv subway
9 yrsIn sales roles before founding PitchMonster
2022The year PitchMonster launched
2Companies built with Mykyta Filipchuk

About Oleg

I started my sales journey at 15, selling Vodafone plans in the Kyiv subways to save up for a mountain bike. Since then, I got addicted to seeing people’s happy faces when they decide to buy or activate something new.

Over the past 9 years, I’ve done all kinds of sales jobs: B2B lead gen in high school, phone sales, partnership and channel sales in SaaS, business development, and organizing offline and online sales conferences. But what really drove me was the desire to build my own product and see those same happy faces using something I created.

With my friend (a very nerdy tech guy), we built Gradual.io. It’s a sales LMS for growing businesses without in-house coaches. It was a cool business. We made our first money, learned how to build a team, talk to customers, and raise funds. But we had limited success with Gradual.

So we interviewed people from Salesforce, Stripe, Zendesk, enablement teams at large enterprises, and sales leaders from SMBs to understand what’s truly painful and still not solved by learning platforms or hundreds of online courses available online.

The answer was simple: practice. That’s how PitchMonster was born. AI role-plays with virtual customers cloned from real buyer profiles, speaking and behaving the way your buyers actually do.

I’m proud we’ve helped people get better at their jobs, earn more, and provide for their families. And we’re just getting started.
Oleg BolotnovFounder & CEO, PitchMonster

What Oleg writes about

  1. AI sales role-playBuilding buyers that push back the way real ones do, and scoring the rep who handles them.
  2. Rep onboarding and rampGetting a new hire from day one to their first real conversation without burning live leads.
  3. Objection handlingThe moments where deals are actually won or lost, and how to rehearse them before they happen.
  4. Sales enablement toolingNine years inside sales orgs, then a sales LMS, then the practice layer the LMS was missing.
  5. Partnership and channel salesSaaS partnerships and business development, the sales motions he ran before building software for them.
  6. Building a sales-led productWhat changes when the founder selling the product is also the one who has to ramp the team.

Why trust Oleg on this

Oleg has run the sales motions he writes about: B2B lead gen, phone sales, partnership and channel sales in SaaS, and business development. He built a sales LMS before building PitchMonster, and shut down the parts that did not work.

The product came out of interviews with people at Salesforce, Stripe and Zendesk, plus enablement teams at large enterprises and sales leaders at SMBs. Every claim about a customer result on this site points at a published customer story, and every competitor claim points at the vendor’s own materials.

AI to Go episode artworkAI to Go Podcast · January 2026This AI is a Better Sales Coach Than YouOleg tells the longer version of the story - real talk on enterprise AI.

What he has built

Founder & CEO

PitchMonster

AI role-plays with virtual customers cloned from real buyer profiles, plus call analysis and coaching.

See the product
Co-founder

Gradual.io

A sales LMS for growing businesses without in-house coaches. First revenue, first team, first fundraise.

Written by Oleg

View all articles
  1. Solution Selling: The Pain Chain, the Buying Committee, and the Sentence Reps Skip
  2. SPICED Sales Methodology: The 5 Elements, and the 2 Stages Reps Have Nothing Rehearsed For
  3. Consultative Selling: Diagnosis Before Prescription, and Why It Collapses Under Pressure
  4. Sales Pitch Training: How to Rehearse a Pitch and a Demo as One Discipline
  5. Sales Negotiation Training: Scenarios, Scripts, and a Rubric Built for Negotiation
  6. Mock Discovery Call Practice: Cadence, Scoring, and a Program That Scales
  7. Sales Training: How to Build a Program That Changes Rep Behavior
  8. Recruiter Training Program: The Call-Drill Build for Agency Teams

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