Services
$480 / month
Start free, decide later
-
1
Free 7-day trial
No charge until day 7. Cancel anytime. -
2
Ongoing calls + chat
3 × 60-min calls per month, unlimited Q&A. Replies in 24 hours or less. -
3
No lock-in
Month to month, no contract.
MentorCruise summary
Oleg is a Founder and AI Product Strategist at ExoChat and Stamina AI. He ran AI product at Intercom from 2019 to 2023 and has founded companies focused on AI implementation. He helps early-stage founders turn ideas into traction, prepare for fundraising, and put AI to work inside their companies.
Based on 3 verified mentee reviews
- Two reviewers praise the value and detailed feedback he brings to meetings.
About
I help two kinds of people: early-stage founders going from idea to first traction, and operators who need AI working inside their company rather than sitting in a slide deck.
At Intercom I ran product for AI from 2019 to 2023: intent detection, resolution bots and workflow automation in the hands of B2B support teams at scale. Before that I was the first product hire at Replyhub, a B2B SaaS in customer support and conversational automation, and a product manager at Paddle. Since then I have founded my own companies, Stamina AI and ExoChat, and worked as an independent AI implementation advisor.
What I have shipped, so you know this is not theory:
• Five AI agents live in production, each doing a specific operational job
• A meeting-notes-to-tasks pipeline deployed org-wide at 200-person scale
• An AI governance pack, usage policy, DPIA, incident playbook and adoption framework, approved by HR and adopted across departments
• Agents, RAG and internal copilots on Claude and OpenAI, measured by cost per task and deflection rate instead of by demo
I work best with:
• Pre-seed and seed founders building B2B SaaS or AI products and getting ready to raise
• Non-US founders looking to crack the US market
• Operators and product leaders rolling out AI inside their company who want an implementation roadmap with owners, dates and a measurement loop, not generic advice
I will not nod along. I will tell you what is distracting you from the real bottleneck and when you are optimising the wrong thing. The founder journey is not linear, and the psychological side matters as much as the product one.
I work in English, Russian and Spanish, and have mentored founders across the US, EU, LATAM and CEE.
Book an intro call or send me a short message about your situation, and we can work out whether I am the right person for it.
What mentees say
5 out of 5 stars
Deleted
Standard Plan • 3 months
My condolences, Derek. It was a pleasure to work with you. Let me know when you are back.
Oleg's response
4 out of 5 stars
Oscar
Standard Plan • 3 months
5 out of 5 stars
Armand
Lite Plan • 3 months
Get to know Oleg
-
Video#138 - AI for Mental Health (Oleg Karakash)
Oleg is an AI enthusiast and mental health advocate; a winning combination for this podcast's hot topic! In this episode, …
Read more
-
Article 5 min readWanting Something Too Much Can Push It Away
Many founders and builders struggle with intense desire: to raise, to grow, to succeed — fast. But sometimes, wanting something …
Read more
What happens when you start
You tell Oleg your goals. They see exactly what you want to work on before session one.
You meet within days. Oleg reviews your application and books your first session, usually within a day or two.
You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.
