You have compelling but invisible positioning. Fifteen years at Stripe and Airbnb creates genuine differentiation in a market full of generic corporate coaches, but zero online presence means prospects can't discover or vet you.
Specific, credible stories from scaling engineering at two of tech's most respected companies
Engineering managers at director-track companies making the EM-to-Director transition
Gergely Orosz's Recommendation List is Kingmaker
His blog post 'Coaches and Mentors for Engineering Managers' is a curated list that drives significant traffic and credibility to featured coaches. Getting listed requires being vouched for by someone he trusts or building enough reputation for multiple recommendations.
Why it matters: Should be a 6-month goal - getting on this list could transform discoverability
Set up Calendly with free "strategy call" booking
Create booking system for discovery calls with clear positioning around EM-to-Director transition
Optimize LinkedIn profile with clear coaching positioning
Update headline, About section, and experience to highlight Stripe/Airbnb background and EM-to-Director coaching focus
Launch simple one-page website this week
Create minimal viable website with positioning, bio, and contact form
Email 3 past clients asking for specific introductions
Systematically ask past clients for introductions to specific people they know who fit your ideal client profile
Write 3-paragraph case study from one client (anonymized)
Document one client's transformation from EM to Director with specific results
Publish first LinkedIn post (Stripe/Airbnb leadership story)
Share specific leadership lesson from Stripe or Airbnb experience using proven template
Document your coaching methodology for website
Articulate your coaching process and philosophy for website and sales conversations
Pitch 5 podcasts for guest appearances
Identify and pitch relevant tech leadership podcasts with your signature stories
3,257 ranking keywords
1,219 ranking keywords
664 ranking keywords
“What upskilling is needed to jump from Engineering Manager to Director of Engineering? I have 16 years experience with 10 years as 100% IC as a developer/senior/lead and the last 6 years as Engineering Manager. I am in between jobs for the last few months, I am targeting Director roles...”
“I used to think coaching was only for people already in the C-suite, but the more I've seen around me, the more I'm convinced it's something mid-level managers and directors should consider.”
“Been promoted to director of engineering. Feeling lonely...”
“Career coach? Worth $11k?”
LinkedIn followers
+100
LinkedIn post impressions (weekly avg)
1,000
Website visitors (monthly)
100
Discovery calls booked
2
Discovery call to proposal rate
50%
Active clients
5
Manager-to-Director Transition Under-served
Most coaching content targets either first-time managers OR C-suite executives. The EM-to-Director gap is discussed heavily on Reddit but has fewer dedicated resources and coaches.
Clear niche positioning opportunity in underserved market segment
Stripe + Airbnb Combination is Rare
Research found many coaches with generic corporate backgrounds or single-company experience. Very few have leadership experience at two of tech's most admired engineering organizations.
This is your primary differentiator - don't bury it in generic positioning
LinkedIn B2B Decision Making
B2B high-ticket purchases are increasingly vetted through LinkedIn profiles. Tech managers Google coaches, then check LinkedIn. A sparse or non-existent profile kills credibility before conversations start.
LinkedIn optimization is not optional - it's table stakes for credibility
Isolation at Director Level
Reddit discussions consistently mention loneliness and isolation when promoted to director level. New directors feel disconnected from peers and miss the support system they had as managers.
Emotional hook for positioning - directors need peer connection and guidance through transition
You have a compelling but invisible business. Fifteen years at Stripe and Airbnb, five satisfied clients from referrals alone, and zero online presence. The good news: your credentials are genuinely differentiated in a market where most coaches have generic corporate backgrounds. The bad news: you're competing against coaches who've spent years building audiences while you've been heads-down delivering.
Your $8K/6-month program is priced appropriately for the market—executive coaching rates range from $200-800/hour, and your program works out to roughly $330/hour assuming bi-weekly sessions. But price isn't your problem. Discovery is. Tech managers actively searching for help with the manager-to-director transition are finding Lara Hogan (13K monthly organic visitors), Reboot.io (3K monthly), and the coaches listed on Gergely Orosz's Pragmatic Engineer blog. You're not in the consideration set because you don't exist online.
The strategy here isn't to out-content people who've been writing for years. It's to leverage what you have—specific, credible stories from scaling engineering at two of tech's most respected companies—and get those stories in front of the right 500 people, not the right 50,000. You need 6-8 new clients per year to hit $100K. That's a relationship-building problem, not a viral content problem.
| Stage | Current State | Gap |
|---|---|---|
| Acquisition | 100% referral-dependent. No website, no LinkedIn, no content. Zero inbound. | No discoverability. Prospects can't find you or vet you. |
| Activation | Unknown—no intake process documented. | No way to convert interest into calls. |
| Retention | 6-month program structure suggests built-in retention. | Unknown completion/satisfaction rates. |
| Referral | Working (5 clients from referrals). | Awkward, inconsistent, not systematized. |
| Revenue | $40K from 5 clients at $8K each. Pipeline empty. | Need 6-8 clients/year for $100K target. |
Tier 1: Large Coaching Organizations
| Competitor | Positioning | Pricing | Traffic | Weakness |
|---|---|---|---|---|
| Co-Active Training Institute | Coach certification + leadership training. 30+ years, 150K+ people trained. ICF accredited. | Certification programs, not 1:1 coaching focus | ~29K/mo | Generic methodology, not tech-specific. They train coaches, not leaders. |
| Reboot.io | "Better humans make better leaders." CEO coaching with psychological depth. Jerry Colonna's firm. | High-end (enterprise + VC-backed founders) | ~3K/mo | Targets founders/CEOs, not the EM-to-Director transition. Very senior focus. |
Tier 2: Solo Coaches with Established Audiences
| Competitor | Background | Approach | Your Advantage |
|---|---|---|---|
| Lara Hogan | Former VP Engineering at Kickstarter. Author of "Resilient Management." | Content-heavy (blog, courses, workshops). Individual coaching available. | You have deeper FAANG-tier company experience (Stripe, Airbnb vs. Kickstarter). |
| Pat Kua | Former CTO of N26. Tech Lead Academy creator. | Newsletter, courses, VP/Director level coaching. | You're more US-market focused; he's Berlin-based. |
| Gergely Orosz | Author of Pragmatic Engineer (1M+ subscribers). | Doesn't coach—but recommends others. | Getting on his recommendation list would be high-value. |
Tier 3: Marketplaces and Platforms
| Platform | Model | Your Consideration |
|---|---|---|
| IGotAnOffer | Coaching marketplace, $100-250/session | Takes significant cut, commoditizes your expertise. Avoid. |
| MentorCruise | Subscription mentorship platform | Lower price point, volume model. Doesn't fit your $8K program. |
| Plato | Engineering leadership community + mentorship | Could be valuable for visibility, not primary channel. |
| Channel | Fit | Investment | Timeline to Results | Priority |
|---|---|---|---|---|
| High | 5 hrs/week | 2-3 months | 1 | |
| Simple Website | High | One-time (8-12 hrs) | Immediate | 1 |
| Podcast Guesting | High | 2-4 hrs/episode + prep | 1-2 months | 2 |
| Newsletter (Substack/LinkedIn) | Medium | 3-5 hrs/week | 6-12 months | 3 |
| Reddit Participation | Medium | 2 hrs/week | 3-6 months | 3 |
| SEO/Blog | Low (near-term) | High | 12-24 months | 4 |
| Paid Ads | Low | High | Unknown | Skip for now |
| Coaching Platforms | Low | Low | Immediate | Skip |
Channel explanations:
LinkedIn (Priority 1): Your buyers are there. Engineering managers at director-track companies have LinkedIn profiles and check them. The algorithm currently favors personal content from real practitioners. Your Stripe/Airbnb stories have built-in engagement hooks. You don't need to go viral—you need 500 right people to see you.
Website (Priority 1): You need a home base for credibility. When someone Googles "[Your Name] coaching," something needs to appear. Keep it simple: who you are, who you help, what you offer, how to book a call. One page is fine. Use Carrd, Webflow, or a simple Squarespace template.
Podcast Guesting (Priority 2): Leverage other people's audiences. Shows like "Developing Dev," "Engineering Leadership Podcast," and "Software Engineering Daily" feature guests with your profile. One 45-minute conversation can reach thousands of your exact target audience. Prepare 3-4 signature stories.
Newsletter (Priority 3): Lower urgency because it takes time to build, but start collecting emails from day one. LinkedIn posts can drive newsletter signups. Don't aim for Gergely's scale—aim for 500 engaged subscribers who match your ICP.
Reddit (Priority 3): Don't sell—participate. Answer questions in r/ExperiencedDevs and r/EngineeringManagers with genuine depth. Over time, you become a recognized name. When you do mention coaching (rarely, contextually), it lands differently.
- Waiting until you have "perfect" content to start. Your stories from Stripe and Airbnb are enough. Write the first draft, publish it, learn from the response.
- Thinking of referrals as awkward asks. Reframe: you're asking satisfied clients to help colleagues who are struggling with the same challenges they faced. Make it about the person being helped, not about you.
- Comparing yourself to coaches who started 5+ years ago. They have audiences you don't. You have recent, specific experience at companies they don't. Different advantages.
- Considering coaching platforms that take large cuts. You're not building a volume practice. Five clients at $8K beats twenty clients at $2K after platform fees—and the positioning is completely different.
- Treating "no online presence" as something to be embarrassed about. You've been doing the work, not performing the work. Now you're making your expertise visible. That's a reasonable sequence.
| Action | Impact | Confidence | Ease | ICE Score |
|---|---|---|---|---|
| Launch simple one-page website this week | 8 | 9 | 7 | 24 |
| Optimize LinkedIn profile with clear coaching positioning | 8 | 9 | 8 | 25 |
| Publish first LinkedIn post (Stripe/Airbnb leadership story) | 7 | 7 | 6 | 20 |
| Email 3 past clients asking for specific introductions | 9 | 8 | 7 | 24 |
| Pitch 5 podcasts for guest appearances | 8 | 6 | 5 | 19 |
| Document your coaching methodology for website | 6 | 8 | 6 | 20 |
| Set up Calendly with free "strategy call" booking | 7 | 9 | 9 | 25 |
| Write 3-paragraph case study from one client (anonymized) | 7 | 8 | 6 | 21 |
| Metric | Baseline (Now) | Week 4 Target | Month 3 Target |
|---|---|---|---|
| Acquisition | |||
| LinkedIn followers | Unknown | +100 | +400 |
| LinkedIn post impressions (weekly avg) | 0 | 1,000 | 5,000 |
| Website visitors (monthly) | 0 | 100 | 400 |
| Discovery calls booked | 0 | 2 | 6 |
| Activation | |||
| Discovery call to proposal rate | Unknown | Track | 50% |
| Revenue | |||
| Active clients | 5 | 5 | 6-7 |
| Pipeline (proposals out) | 0 | 1-2 | 3-4 |
| Referral | |||
| Referral requests sent | Unknown | 5 | 10 |
| Referrals received | Unknown | 1-2 | 3-4 |
Template 1: The Stripe/Airbnb Insight Post
Format: Story → Lesson → Question
At [Stripe/Airbnb], I watched dozens of engineering managers try to make the jump to director.
The ones who succeeded all did one thing differently:
[Specific observation—be concrete]
Here's what I mean:
[2-3 sentence example]
The ones who stayed stuck?
[Contrast behavior]
If you're an EM eyeing that director role, ask yourself:
[Provocative question related to the insight]
---
I coach tech managers making this exact transition. If you're feeling stuck, let's talk. Link in bio.Example:
At Stripe, I watched dozens of engineering managers try to make the jump to director.
The ones who succeeded all did one thing differently:
They stopped solving problems and started naming them.
Here's what I mean:
A strong EM sees a delivery risk and fixes it. A director-ready EM sees the same risk, names the pattern across teams, and brings it to leadership as an organizational issue—with options.
The ones who stayed stuck?
They kept being the best problem-solver in the room instead of the person who helped the room see problems differently.
If you're an EM eyeing that director role, ask yourself:
When's the last time you brought a problem UP instead of solving it DOWN?Template 2: The "What I Wish I'd Known" Post
Format: Past mistake → What happened → What I learned
When I first became a director, I made a mistake that cost me six months of credibility.
[What you did]
It seemed like the right move at the time because [reasoning].
But here's what actually happened:
[Consequence]
What I learned:
[Lesson, stated simply]
If you're stepping into director for the first time, remember: [one-sentence takeaway].
---
I help engineering managers navigate this transition. DM me if you want to talk.Template 3: The Contrarian Take
Format: Common belief → Why it's wrong → What to do instead
Unpopular opinion about the EM to Director path:
[Common advice] is actually holding you back.
Here's why:
[Explanation—ideally with specific example]
What works better:
[Alternative approach]
I've seen this play out at Stripe, at Airbnb, and with the managers I coach.
The directors who rise fastest aren't the ones who [common behavior].
They're the ones who [contrarian behavior].Final Note: The strategy here is deliberately focused. You don't need a podcast, a course, a book, and a massive email list. You need 6-8 people per year who trust you enough to pay $8K for your help. Everything in this plan points toward that: being visible to the right small audience, being credible when they check you out, and being easy to reach when they're ready.
Execute the first four weeks. Then we can talk about what's working and adjust.