Milestone map
Milestone map
3 milestones
Identify and systematise the $100K ARR motion
2–3 weeks (analysis)
You cannot reach $1M ARR by doing something new — you reach it by doing more of exactly what got you to $100K. Before scaling, document the revenue motion that generated your first $100K in annualised recurring revenue: which channel, which ICP, which deal size, and which value proposition. Identify the three activities that most directly drove that revenue and calculate how many repetitions of each would get you to $1M ARR. This is your scaling hypothesis.
Proof required
Submit: (a) a one-page revenue motion analysis showing the source of your first $100K ARR (channel breakdown, ICP profile, average deal size); (b) your three core revenue-generating activities with the weekly cadence you ran them at to reach $100K; and (c) your scaling hypothesis — how many weeks of those activities at what expanded cadence equals $1M ARR.
What gets checked
- Revenue breakdown is from your accounting or billing tool, not estimated — cite the source.
- Three core activities are specific and repeatable (e.g. '20 outbound emails per day targeting VP Engineering at 50-200 person SaaS companies'), not vague ('outreach').
- Scaling hypothesis includes a realistic timeline that accounts for diminishing returns at higher cadence — not linear extrapolation.
Common mistakes
- Assuming the motion that got you to $100K will get you to $1M unchanged — it usually won't, and identifying where it breaks is the goal.
- Analysis based on revenue memory rather than billing tool data — introduces errors that make the hypothesis unreliable.
- Scaling hypothesis that just multiplies the current team's capacity — doesn't account for hiring, process, and efficiency changes.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the founder to describe the single activity that would most directly move the ARR number this week — vague answers mean the motion isn't documented enough to execute.
- Ask whether the scaling hypothesis assumes linear or diminishing returns and why — the answer reveals how carefully it was thought through.
- Check that the revenue breakdown references a real billing system, not founder recollection.
Build the operational infrastructure for scale
6–10 weeks (building and testing each process)
$1M ARR requires processes that work without the founder doing everything. Build and document: (a) a customer success process (what happens after a customer signs — onboarding, QBR, renewal); (b) a sales handoff process (how a deal moves from founder-sold to first sales rep-sold); (c) a repeatable demand generation engine with a defined weekly output (leads, content pieces, outreach volume). For each, produce a written SOP and evidence that you've run it at least twice without doing it yourself.
Proof required
Submit your three SOPs, evidence that each ran at least twice with someone other than the founder executing (e.g. a team member's execution log, a CRM screenshot showing activities by a non-founder), and a one-paragraph note on what you had to fix after the first non-founder execution of each.
What gets checked
- Each SOP is specific enough that a new hire on day one could execute it — vague 'reach out to customers regularly' instructions are not SOPs.
- Evidence of non-founder execution is documented, not stated — CRM records, task completion logs, or equivalent.
- Fix note names the specific breakdown that occurred in the first non-founder execution — 'it went fine' means the SOP wasn't tested properly.
Common mistakes
- Writing SOPs but not testing them with someone else — you find out what's missing only when someone else tries to follow it.
- Customer success SOP that doesn't have a renewal trigger — you'll lose customers at contract end without a systematic renewal process.
- Treating founder-led sales as not repeatable — it must be documented even if imperfectly, or you can't hire the first sales rep.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the founder to hand over one SOP and walk you through the most recent execution — you're checking whether the SOP matches what actually happened.
- Ask what broke in the first non-founder execution of each process and what they changed.
- Ask what would happen to the customer renewal rate if the founder were unavailable for 4 weeks — the answer reveals how complete the customer success SOP is.
Cross $1M ARR with documented evidence
6–18 months from $100K ARR (highly variable)
Reach $1M in annual recurring revenue (not annual contract value, not gross revenue — ARR from subscription or contract renewals). Produce a one-page ARR milestone document showing: the date you crossed $1M ARR, the customer count and average deal size at that point, the channel breakdown of how revenue was acquired, your net revenue retention, and a one-paragraph reflection on what you now know about your market that you didn't know at $100K ARR.
Proof required
Submit a screenshot or export from your billing/subscription management tool showing the date and total ARR crossing $1M, your ARR milestone document, and a one-paragraph reflection on the market insight you've gained.
What gets checked
- ARR is from subscription or recurring contract revenue — not one-time payments, not projected ARR from pilots.
- Billing tool evidence shows the exact date ARR crossed $1M — not an estimated date.
- Market insight reflection names something specific that changed your understanding of the customer, competitor landscape, or go-to-market motion — not a general 'we learned a lot' observation.
Common mistakes
- Counting annual contract value for multi-year deals without confirming renewal is contractual — ARR requires recurring revenue, not committed spend.
- Crossing $1M ARR but not documenting the channel breakdown — the channel data is what tells you where to invest next.
- Reflection that describes the growth story rather than a genuine insight — the insight should be something the founder would have found counterintuitive at $100K ARR.
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the founder to show the billing tool export with the date ARR crossed $1M — the date must be traceable to a real system record.
- Ask what the net revenue retention is — NRR above 100% is a signal of a healthy $1M ARR business; below 90% means churn is a critical issue at this stage.
- Ask what the most counterintuitive thing they now know about their market is — if the answer could have been known before building the business, it's not a genuine insight.
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