Entry 001 — The problem

Nobody owns the middle.

Marketing owns the traffic. Sales owns the demo. Product owns the app. The stretch between a self-serve signup and a closed deal belongs to no one — so users quietly get stuck there, and the growth you paid for slips away.

That gap is a product problem, not a marketing one. I find where your users are quietly struggling, work out why, and turn it into changes your team will actually ship — through real research, not another dashboard.

Start with a $2,500 diagnostic See how I work Score your funnel — free
002Pattern

If you're between $1M and $8M, I can guess three of your problems.

Not because your product is generic — because the shape of this stage is. Here's what shows up almost every time.

Pattern 01 · Activation

Your signup is good. Your first ten minutes are not.

Teams optimize the form and then hand new users a blank workspace. The number that predicts retention isn't signups — it's the share of people who reach a first real win, and almost nobody measures it.

Pattern 02 · The handoff

Self-serve and sales are two separate products wearing one logo.

A trial user who wants to talk to someone hits a contact form. A sales lead who wants to poke around gets a demo booking. Both are asked to behave like the other kind of buyer.

Pattern 03 · The silent churn

You know who cancelled. You don't know who decided to.

The decision to leave happens weeks before the cancellation, usually at a moment of friction nobody logged. By the time it shows up in the numbers, the conversation that would have explained it is long over.

If two of those landed, that's the work. If none did, you probably don't need me — and I'd rather say that early.

003Method

Every finding takes the same shape.

What I saw. What I think is causing it. What to test. I don't assert anything I haven't observed, and I don't recommend anything you can't measure.

The climb from “account created” to “first booking” is too steep
S-C2
Observation

The most consistent theme across user reviews is a steeper learning curve than the incumbent. After signup a new user must connect a calendar, configure availability, and build an event type before reaching a shareable link that produces a real booking. Every one of those is a place to stall.

Hypothesis to test

An opinionated first run — one-click calendar connect, a default event type, sensible default availability, an instantly shareable link — lifts activation, and therefore retention.

Impact: High Effort: Medium Stage: Activation

From the Cal.com teardown. I publish one of these every couple of weeks — a full outside-in read of a real product in this space, same method as a paid engagement, no pitch attached. Read the Cal.com teardown →

004Scope

Who this is for.

Built for one specific situation. If you're not in it, you'll get more from someone else, and I'll tell you that on the first call rather than after the invoice.

A fit

  • B2B SaaS, roughly $1–8M ARR
  • A free trial or self-serve signup and a sales team
  • Nobody whose actual job is signup to revenue
  • Enough traffic to run a test and read the result

Not a fit

  • Pre-revenue or still hunting for product-market fit
  • Fully sales-led, no self-serve motion
  • An in-house growth team already owns this
  • Looking for hands to execute, not a diagnosis
005Straight answers

The questions founders actually ask me.

Why not just hire a growth PM?

Eventually you should. But that's a $180k commitment and a three-month search, and you'd be hiring against a problem you haven't diagnosed yet. Do the diagnosis first — then you know what to hire for, and the person you hire has a roadmap on day one.

We already have Amplitude. Isn't this the same thing?

Analytics tell you where people drop off. They can't tell you why, because the answer isn't in the data — it's in the head of the person who left. That's what the interviews are for. I use your analytics; I just don't stop there.

How is this different from a growth agency?

Agencies mostly run acquisition — ads, SEO, outbound — and get paid to send you more traffic. I don't touch acquisition. I work on what happens after someone arrives, which is usually the cheaper problem and almost always the one nobody's looking at.

Will this turn into a slide deck nobody reads?

Fair worry, and it's the normal outcome. Which is why the deliverable is a ranked queue of testable changes with effort estimates, handed over in a working session with the people who'd build them — not a PDF emailed to the founder.

How much of my team's time does this take?

About three hours total: a kickoff, read-only access to your analytics, and one session at the end. I handle the customer interviews myself, including the recruiting.

006Practice

Analytics tell you where. Research tells you why.

Most growth work stops at the funnel chart — which is why most growth work produces the same twelve recommendations.

I started in UX research before moving into product, and spent five years as a senior product manager across SaaS, cybersecurity, and field-service software. That order matters. I learned to sit with a customer and hear the thing they didn't quite say before I ever learned to read a cohort chart. A drop-off point is a symptom. The interview is where the cause is.

So every engagement runs both. The numbers find the gap, the conversations explain it, and what comes out the other side is a recommendation your product team actually believes — which is the only kind that ever ships.

A few results from that work:

  • Took a product from zero to $1M ARR in eight months.
  • Lifted retention 10% by building re-engagement into the customer journey.
  • Drove 15% growth in conversions across multiple markets through targeted feature changes.
007The work

Three ways in. Start small.

You shouldn't have to commit five figures before you've seen me be right about something. So the first step is small, fast, and credited back if you go further.

The Diagnostic

$2,500 · 1 week

An outside-in read of your funnel — no access needed, nothing for your team to prepare. You'll know within a week whether there's real money sitting in your middle, and roughly where.

  • The five biggest opportunities I can see from outside, ranked
  • A scored read across six dimensions, benchmarked against comparable companies
  • A 45-minute call to walk you through it and argue with me
  • Delivered in five working days
  • Outside-in only — the deeper in-product drop-off analysis comes with the Audit
The full $2,500 is credited if you move to an audit. If you don't, you keep the findings and owe me nothing else.

The Growth Audit

$9,500 · 3 weeks

Everything the diagnostic guesses at from outside, answered from inside — with your data and your customers.

  • Full read of the path from first visit to closed revenue — site, signup, activation, pricing, the handoff to sales
  • Exactly where users drop off inside the product — onboarding, first-run, and the in-app flows where they stall — from your analytics and real user conversations, not guesses
  • Four to six interviews with your users, churned users, or lost deals — synthesized, not transcribed
  • Every finding as observation → hypothesis → experiment, ranked by impact against effort
  • A 30/60/90 plan and a live experiment queue your team can pick up on day one
  • A 90-minute working session to walk the team through it
One week in, if I don't think there's real money to be found, I stop and refund you in full. I'd rather lose the fee than write a report nobody needed.

The Growth Partnership

$6,500/mo · 6 months

The audit tells you what to fix once. The partnership makes sure you always know what to fix next.

  • A monthly read on your in-product drop-offs — what moved, what regressed, and what to fix next
  • A quarterly research cycle — real conversations with real users
  • A maintained experiment queue: hypothesis, status, result
  • A monthly working session with your product team

Half the audit fee is credited against your first three months if you continue into a partnership.

008Start

Where do you think you're losing them?

Tell me that in two sentences. I'll tell you on a 30-minute call whether this is worth your money — or whether the answer is something simpler you can do yourselves.

Book a 30-minute call
Free · 2 minutes · no access needed

How much is leaking in your middle?

The stretch between a self-serve signup and a closed deal belongs to no one — which is exactly where the revenue goes. Score your own funnel across six dimensions and see where yours is losing people.

Score my funnel Have me read your live site instead
001  The scorecard

Score your funnel in two minutes.

Answer honestly, from your customer's point of view. I'll weight the score to your motion — the same six dimensions I use in a paid diagnostic.

First — what's your go-to-market motion?
Product-led
Users sign up and self-serve. No sales touch to start.
Self-serve + sales
Both motions — the “middle.” Bearing True's home turf.
Sales-led
Demos and sales calls drive most revenue.
Please pick your motion and answer every question to see your score.
0/100
—

See your six-dimension read + your three biggest leaks

Two fields to unlock your full breakdown and the highest-leverage places to look first.

First name
Work email
Company
Website
Please enter your name and a valid work email.
—  Where to look first
The Diagnostic · $2,500 · 1 week

This is your self-scored guess. Want mine — from the outside?

A Bearing True Diagnostic is an outside-in read of your real funnel: the five biggest opportunities I can see, ranked, scored across these six dimensions and benchmarked against comparable companies — in five working days, no access needed. Credited in full if you move to an audit.

Start with a $2,500 diagnostic
002  Prefer I do it

Have me read your live site.

Skip the self-score. Leave your details and I'll run a short outside-in read of your real funnel and send back two or three specific findings — free, no pitch attached.

First name
Work email
Company
Your role
Website to read
Please enter your name, a valid work email, and your website.
✓ Got it — I'll read your funnel and send a few specific findings shortly.
Public, outside-in observation only. No access, no passwords, ever.
Entry — The Cal.com teardown

Cal.com wins the signup, then makes you earn the first win.

A public, outside-in read of a well-positioned PLG product. Strong differentiation and trust get people in the door; the leak is in the climb from “account created” to “first real value.”

Target: Cal.com — B2B PLG scheduling SaaS Read: Aug 2026 Type: Outside-in · public observation
001  Method

What I saw. What I think is causing it. What to test.

Every finding takes that shape. I don't assert anything I haven't observed, and I don't recommend anything you can't measure.

This is an outside-in read — the live site, pricing, real signup flow, docs, and third-party user reviews. No account was created and no analytics were accessed, so activation and retention findings are evidence-backed hypotheses, not internal funnel numbers. Quantifying them is what a full audit (with your data and your users) is for.

002  The read

Strong at the door, thin in the middle.

Cal.com has a rare asset: real differentiation (open-source, own-your-data, developer-extensible) and a top-tier trust stack. Signup is friction-light and well-merchandised. The gap opens after signup — reviewers describe a steeper learning curve than the incumbent, and the path to a shareable link that produces a booking runs through calendar OAuth, availability, and event-type setup. In PLG, time-to-value predicts retention. That's the leak.

71/100
Solid but leaking

Good bones and a genuine moat — trapped value concentrated in activation.

—  Six-dimension read
First impression & positioning78
Signup, activation & the handoff68
Pricing & packaging65
Trust & social proof85
Clarity & education66
Retention & expansion64

Scored on the Bearing True six-dimension rubric (0–100, qualitative). The one-line version: the differentiation and trust are doing the hard work of getting people in — the opportunity is to stop making them earn their first win.

003  Findings
01 · First impression & positioning
The hero never answers “why should I switch — or sign up at all?”
S-A1
Observation

The homepage leads with “The better way to schedule your meetings” — a category line any competitor could run. From a visitor's seat, it never answers the only two questions that matter at first glance: why switch, and why you over Calendly? The real wedge — open-source, own your data, developer-extensible — is on the site but not led with. The hero also serves individuals, teams, orgs, enterprise and a stack of verticals at once, diluting it further.

Hypothesis to test

A hero that states the switch/sign-up reason explicitly and up front, plus segment-specific landing paths, lifts qualified signups from switchers versus the catch-all headline.

Testimonials from Vercel & Supabase founders praise leaving Calendly — the switch story is the real wedge, under-used up top.
Impact: HighEffort: Low–MedStage: Positioning
02 · Signup, activation & the handoff  · the money path
Signup is genuinely excellent — protect it
S-C1
Observation

SSO-first (Google, Microsoft, email, SAML), a credible social-proof rail (Product Hunt #1, G2, Google stars), and a live product preview. A real strength worth naming. One minor edge: the email path enforces only a 7-character password minimum — below the modern 8+ norm and slightly off-brand for a product that sells SOC 2 / HIPAA / ISO trust.

Impact: Low (trust)Effort: Low
The climb from “account created” to “first booking” is too steep
S-C2
Observation

The most consistent theme in reviews is a steeper learning curve than the incumbent. After signup a new user must connect a calendar, configure availability, and build an event type before reaching a shareable link that produces a real booking. Every one of those is a place to stall — and the share of users who reach first value is the number that best predicts 30-day retention.

Hypothesis to test

An opinionated first run — one-click calendar connect, a default event type, sensible default availability, an instantly shareable link — lifts activation, and therefore retention. The highest-leverage finding here.

Review themes: “steeper learning curve than Calendly,” “rough edges because it moves fast.” Satisfaction tracks whether users expected a zero-config clone.
Impact: HighEffort: MediumStage: Activation
The username step is a smart touch that can also stall people
S-C3
Observation

Email signup asks the user to claim a cal.com/username up front — good, because the link feels owned immediately, but a naming decision at signup is a place indecisive users pause.

Hypothesis to test

Auto-suggesting a username (from name/email) with easy edit reduces drop-off without losing the ownership benefit.

Impact: Low–MedEffort: Low
03 · Pricing & packaging
Prices don't match across pages
S-P1
Observation

The homepage snapshot shows Teams $16 / Organizations $37 per user/mo; the pricing page shows $12 / $28. Likely monthly-vs-annual — but a visitor who sees two numbers for one plan reads it as inconsistency, right at the upgrade moment.

Hypothesis to test

One consistent price everywhere with a clear monthly/annual toggle reduces hesitation and pricing support load.

Observed: homepage “Teams $16 / Orgs $37” vs pricing page “Teams $12 / Orgs $28 (annual).”
Impact: Med–HighEffort: Low
Four tiers plus verticals invite choice overload
S-P2
Observation

Free, Teams, Organizations, Enterprise — plus vertical variations — is a lot for an SMB buyer to reason about, with no strong “most teams choose this” anchor.

Hypothesis to test

A recommended-plan anchor and a clearer free→Teams story lift free-to-paid conversion.

Impact: MediumEffort: Low
04 · Trust & social proof
Trust is a moat — surface the compliance proof where it closes deals
S-T1
Observation

Founder testimonials, Product Hunt badges, G2, open-source credibility, SOC 2 / HIPAA / ISO. Excellent. The refinement: for the org and healthcare ICPs where compliance is a deal-maker, that proof is buried in the pricing tiers rather than surfaced where those buyers land.

Hypothesis to test

Elevating security/compliance proof on org- and healthcare-intent pages shortens the enterprise consideration cycle.

Impact: MediumEffort: Low
05 · Retention & expansion  · the recurring-revenue engine
“Moves fast, rough edges” is a retention risk on the daily-use surface
S-R1
Observation

Reviewers note the product moves fast and can feel less polished than incumbents. For a tool used daily on the booking path, polish is what keeps a switcher from switching back.

Hypothesis to test

A focused reliability pass on the core booking-and-calendar path protects retention more than shipping features in the same period.

Impact: High (retention)Effort: Med–High
Free-tier users lean on docs — and they're the future expansion revenue
S-R2
Observation

Dedicated support is reserved for higher tiers; free users rely on community and docs. But free users are the top of the funnel and the seedbed of team expansion — a rough self-serve moment can end it before it monetizes.

Hypothesis to test

Lightweight in-product self-serve help at known friction points improves free→paid conversion without adding support cost.

Impact: Med–HighEffort: Medium
The solo→team expansion trigger is left to the user
S-R3
Observation

The freemium→Teams motion exists (round-robin, shared availability) but expansion waits for the user to discover it. When a solo user acts team-shaped, nothing surfaces the team value.

Hypothesis to test

Behavior-triggered expansion prompts (invites, collaboration limits) lift free→Teams conversion.

Impact: High (expansion)Effort: Medium
004  Ranked

Ten opportunities, by impact × confidence ÷ effort.

#OpportunityImpactEffortRef
1Ship an opinionated, guided first-run — one-click calendar, default event type & availability, instant link.HighMedS-C2
2Answer “why switch / why sign up” up front — lead the hero with the wedge + segment paths.HighLow-MedS-A1
3Fix price inconsistency across pages; one number + clear monthly/annual toggle.Med-HiLowS-P1
4Behavior-triggered solo→Team expansion prompts.High*MedS-R3
5Reliability/polish pass on the core booking & calendar path.High*Med-HiS-R1
6In-product self-serve help for the free tier at known friction points.Med-HiMedS-R2
7Auto-suggest (skippable) username at signup.Low-MedLowS-C3
8“Most teams choose this” plan anchor; sharpen the free→Teams story.MedLowS-P2
9Surface SOC 2 / HIPAA / ISO proof on org- & healthcare-intent pages.MedLowS-T1
10Raise the password minimum to 8+ to match the security positioning.LowLowS-C1

*High impact realized over a retention/expansion horizon. Activation is #1 because in PLG it compounds into every downstream metric.

005  First tests

What I'd run first — once activation is instrumented.

E1 · Guided first-run vs. current onboarding
Ship the opinionated setup to half of new signups. Win: higher % reaching activation — calendar connected + first event type + link shared within 24h.
E2 · Wedge-led hero vs. category hero
Differentiator-led headline + segment paths. Win: higher qualified-signup rate and signup→activation carry-through.
E3 · Consistent pricing + billing clarity
Align homepage and pricing page. Win: higher upgrade CTR, fewer pricing tickets.
E4 · Behavior-triggered expansion prompt
Surface team value when solo users act team-shaped. Win: higher free→Teams conversion.
Step 0 is instrumentation. None of these can be judged without an activation funnel: signup → calendar connected → availability set → first event type → link shared → first booking received.
006  Sequence

A 30 / 60 / 90-day plan.

Days 0–30

Instrument + quick wins

  • Instrument the activation funnel end-to-end
  • Fix cross-page price inconsistency
  • Raise password minimum to 8+
  • Surface compliance proof on org pages
  • Auto-suggest username at signup
Days 31–60

Attack time-to-value

  • Guided, opinionated first-run
  • Wedge-led hero + segment paths
  • “Most teams choose this” anchor
  • In-product help at top friction
Days 61–90

Retention & expansion

  • Behavior-triggered solo→Team prompts
  • Reliability pass on core path
  • Read activation→retention lift, iterate
  • Shift to a monthly cadence
007  What's next

This teardown found the friction from outside. The next read is from inside.

With read-only analytics and a handful of user conversations, the same method produces quantified priorities — not hypotheses. Three ways in:

The Diagnostic

$2,500 · 1 week

An outside-in read like this one, on your funnel — five biggest opportunities ranked, scored across the six dimensions, benchmarked. Credited in full if you move to an audit.

The Growth Audit

$9,500 · 3 weeks

Everything the diagnostic guesses at from outside, answered from inside — your data, four to six user interviews, every finding as observation → hypothesis → experiment, a 30/60/90 and a live experiment queue.

The Growth Partnership

$6,500/mo · 6 months

The audit tells you what to fix once. The partnership makes sure you always know what to fix next — monthly reads, a quarterly research cycle, a maintained experiment queue.