GTM Career Mentorship
The jump nobody explains.
1:1 mentorship for GTM professionals moving from individual contributor to team lead, team lead to senior leadership, or into GTM from a different career altogether — including the parts nobody prepares you for, like the imposter syndrome that comes with each jump.
Who this is for
The moves nobody explains
None of this is specific to sales or GTM. If you're navigating one of these in engineering, product, design, or anywhere else, the underlying problem is the same.
You're one of the strongest individual performers on the team, but the promotion case feels vague, and nobody's told you what actually separates a strong IC from someone ready to lead one.
We work through the real evidence a promotion needs: how you already coach peers, how repeatable your process is, and how to make that case explicitly instead of hoping it gets noticed.
You got the promotion, and now the people who used to be your equals report to you. The friendships feel different, decisions feel heavier, and nobody prepared you for the first 90 days of this.
We work through resetting the relationship deliberately: what to say in the first two weeks, how to lead without over-explaining yourself, and how to stop trying to out-perform your own team to prove you deserve the seat.
You're running a team well, but the jump to VP or Head-of needs a different kind of credibility, forecasting, org design, cross-functional influence, that managing your own team doesn't teach you.
We work on the specific gaps: building a board-ready narrative, operating beyond your own function, and being visibly ready before the role even opens up.
You're moving into a new function, sales, customer success, GTM, or somewhere else entirely, and it's hard to tell which of your existing skills actually transfer, and which gaps are real.
We map what you already bring, close the specific gaps that matter for the roles you're targeting, and build a story that makes sense to a hiring manager who's never seen your background before.
A note on imposter syndrome: every one of these moves comes with a stretch of feeling like a fraud. Most people are promoted into leadership because they were excellent at their previous job, not because anyone taught them how to lead, this is sometimes called the "accidental manager" problem, and it's the norm, not the exception. That's not a sign you're in the wrong place. We deal with the practical gaps and the feeling at the same time, not one before the other.
About
15+ years building and leading revenue teams
Shash Tandon
GTM Career Mentor · Prague
I've spent the last 15 years in B2B SaaS sales, customer success, and go-to-market strategy, hiring, promoting, and mentoring the people who make those functions work. Engineering background, MBA in finance, and a habit of getting closer to the technical buyer than most commercial leaders bother to. I mentor GTM professionals through the two hardest jumps in the career, IC to team lead, and team lead to senior leadership, plus the move into GTM from somewhere else entirely.
- Head of Sales, Proton — scaled the B2B team from 1 to 10+, eight consecutive quarters over target.
- Senior Enterprise CSM, Productboard — 125% net revenue retention across an enterprise book.
- Head of Customer Experience, wflow — built onboarding, account management, and support from scratch.
- GTM Advisor, Apify — built the go-to-market team from scratch.
- GTM Advisor, Resistant.ai — built the go-to-market team from scratch.
- B.Tech, Electrical & Electronics Engineering and an MBA in Finance.
Based in Prague, working across Europe — primarily CEE, Germany, the Netherlands, and the Nordics.
Mentorship
Three tracks, structured around where you are
No published pricing here on purpose — the right cadence depends entirely on what you're working through. Let's talk first.
Team Lead Readiness
Build the case, and the actual skills, for moving from top individual performer to someone ready to lead a team.
Senior Leadership Coaching
Close the strategic and cross-functional gaps between running a team and being trusted to run a function.
GTM Career Transition
Map what already transfers from your current background, close the real gaps, and build a story that lands with hiring managers.
FAQ
Common questions
How do I know if I'm ready to move from individual contributor to team lead?
Strong individual performance is necessary but not sufficient. The signals that usually matter more: whether you already informally coach or unblock peers, whether you can explain your own process clearly enough for someone else to repeat it, and whether you're motivated by team outcomes as much as your own number. If those aren't there yet, that's exactly what to build before the move, not after it.
What actually separates a strong individual contributor from someone ready to lead a team?
Performing the job well and being ready to lead people who do the job are genuinely different skill sets. The clearest signal is whether you can turn your own instincts into something teachable: a process, a framework, a way of coaching, rather than just doing the work faster or better yourself.
What skills matter most moving from team lead to senior GTM leadership?
The jump from team lead to VP or Head of typically requires strategic and cross-functional skills that managing your own team doesn't teach on its own: forecasting and board-level reporting, org design, hiring at scale, and influence across product, marketing, and finance rather than just your own function.
Is imposter syndrome normal when moving into a leadership or GTM role?
Yes, and it's one of the most consistent things people report at every one of these transitions. It's not usually a sign you're in the wrong role, it's the ordinary cost of doing something you haven't done before. The useful move is separating the feeling from the facts: naming exactly what skill or evidence is actually missing, versus what's just unfamiliarity.
How do I manage people who used to be my peers?
Have a deliberate one-on-one reset conversation with each former peer early rather than letting the relationship redefine itself through silence. Be explicit about your decision-making style and standards instead of assuming it's understood. And resist the instinct to out-produce your own team to prove you deserve the promotion, your job changed from doing the work to making everyone else better at it.
Does this only apply to GTM, sales, or customer success roles?
My own background is GTM and revenue leadership, so that's where my examples and pattern-matching are deepest. But the core of this work, building a promotion case, learning to lead instead of just perform, managing former peers, closing the confidence gap, isn't specific to any one function. If you're facing the same jump in engineering, product, or elsewhere, it's still worth a conversation.
I'm changing careers into sales, customer success, or GTM from a different background. Where do I start?
Start by mapping which of your existing skills genuinely transfer, communication, problem-solving, domain expertise, and which gaps are real and need to be closed before you're a credible candidate. Most career changers either undersell what already transfers or try to compete on GTM-specific experience they don't have yet. Both are fixable once they're named clearly.
Which of my existing skills actually transfer into a GTM role?
It depends heavily on your background, but the common transferable skills are structured communication, handling objections or resistance, technical or domain fluency if you're coming from a specialist field, and any prior experience managing relationships or expectations. The gap is usually GTM-specific process and vocabulary, which is learnable faster than most career changers expect.
What does a mentorship session actually look like?
1:1 conversations focused on a specific, real situation: a promotion case you're building, a deal or team problem you're stuck on, or a move you're actively considering. It's practical and tied to your actual work, not a fixed curriculum.
Are sessions one-off or ongoing?
Both exist. Some people need a single focused conversation before a decision or a negotiation. Others want an ongoing cadence through a longer transition. The free 15-minute call is there to figure out which one fits before committing to either.
Do you work with people outside the Czech Republic?
Yes. Based in Prague, working remotely across Europe, primarily CEE, Germany, the Netherlands, and the Nordics, with sessions conducted in English.
How much does mentorship cost?
It depends on the scope, a single session and an ongoing engagement are priced very differently. The most useful next step is a short call to figure out what you actually need before talking about cost.
Get in touch
Tell me what you're working on
A couple of lines is enough. I'll follow up directly, or you can skip straight to booking a call above.
Thanks — I'll get back to you directly.