Twelve-Month Payback Challenge

What You'll Be Doing

Wickfield closed a Series B. The board attached a condition: blended CAC payback drops from 19.4 months to 12 months or better within two quarters, while net new ARR grows at least 25% quarter over quarter. You run growth. This is your plan.

The economics as they stand:

Total S&M last quarter: $4,119,000. New paid accounts: 1,973. Blended CAC $2,088.
Gross profit per account per month: $107.64. Payback: 19.4 months.
S&M breaks down as: paid media $929,000; content team and tooling $190,000; agent pipeline $4,200; sales team $1,996,000 (22 AEs, fully loaded); everything else $999,800.

By segment:


Segment	% of new accounts	ARPA	12-mo retention	Motion
Sole-proprietor contractors	64%	$79	52%	Self-serve
Multi-location / dental	22%	$312	88%	Sales-assisted, 41% close rate
Small agencies	14%	$196	71%	Mixed

Two pieces of evidence you already have:

Brand search costs $88,000 a quarter at a 1.3-month payback. A two-week brand-search holdout in one metro showed 71% of brand conversions happened anyway.
AI answer engines now drive 11% of trial starts, up from 0.6% a year ago. Those trials convert to paid at 9.4% against 6.2% for the rest of organic.

Write the plan and make the call.

Constraints to consider

Two quarters. The budget cannot increase. And you cannot hit the payback number by simply spending less, because the board also requires ≥25% quarter-over-quarter net new ARR growth.
You cannot reduce sales headcount this quarter. Retaining the AE team was a commitment made at the raise.
Any segment you deprioritize must come with a stated re-entry condition. The CEO founded this company for contractors and will not accept a plan that reads as abandoning them.
The agent pipeline can be expanded, but marketing gets no engineer. Anything you build has to be operable by a four-person team.
You present this to the board, the CFO, and a co-founder who believes payback targets are how companies stop growing.

AI Usage Guidance

We expect you to use AI tools. We evaluate how you use them — not whether you use them. Evidence of iteration, redirection, and critical evaluation scores higher than a polished output with no process documentation.

The single highest-signal indicator: your video answer to the mandatory AI question. If you cannot name a specific moment where you redirected AI output, evaluators will assume you did not.

Mandatory AI question for your video: Walk me through one moment where you disagreed with, pushed back on, or redirected what the AI gave you — and what you did instead. Name the specific moment. Explain what the AI produced that didn’t meet the bar, what you did differently, and why.

Communication clarity matters for this role. We assess structure, stakeholder awareness, and ability to simplify complex ideas — not presentation style or accent.

What You'll Accomplish

Rebuild a company’s acquisition economics against a hard target using segment-level arithmetic

Reason explicitly about the tension between an efficiency mandate and a growth mandate

Sequence incrementality evidence so each test unblocks a specific decision

Design an agent-powered system a four-person team can actually operate, with a guardrail

Defend an unpopular plan to a board audience that includes a committed skeptic

How Your Work Will Be Scored

Channel & Segment EconomicsAI Leverage & System Design Strategic Judgment & Risk Video Walkthrough & Executive Communication AI Fluency

What to Submit

File 1 — Payback Plan

Document · 2 pages maximumRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Your recommendation, the segment and channel moves behind it, and the arithmetic that gets from 19.4 months to 12 or better while holding ≥25% QoQ net new ARR growth. Show the numbers.

File 2 — README Document

DocumentRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Three required sections:

Section A — Written analysis: the tradeoff argument with the numbers attached. What you are trading against what, what the plan costs in growth, and the strongest case against it. 350–450 words.
Section B — Evidence, system, and the number on the wall:
1. The measurement plan — the incrementality tests you would run, in what order, what each costs in foregone conversions, and the specific decision each one unblocks.
2. The system — the agent-powered workflow you would build, what it replaces, what it costs to run, and the guardrail that keeps it from producing something you would have to apologise for.
3. The one number you would put on the wall for the quarter, and why it is that one rather than blended payback.
Section C — AI Usage Log (Mandatory): This is not a trick. We want to see how you work with AI — not whether you used it. In a short section of your README, document your AI collaboration process. For each significant interaction with an AI tool, briefly note: what you asked the AI to help with / what it gave you / what you kept, changed, or rejected — and why. Three interactions documented is sufficient. The log does not need to be exhaustive.

File 3 — Video Walkthrough

Video · 6-8 minutesRequired

Format: .mp4, .mov, .webm

Record as MP4 or MOV and upload directly on the Provn platform as a separate file. Cover: (1) your recommendation and the arithmetic, ~60 sec; (2) the segment and channel moves, ~2 min; (3) the measurement plan and the system you’d build, ~90 sec; (4) how you answer the co-founder who thinks payback targets kill growth, ~60 sec; (5) the mandatory AI question, ~60 sec; (6) what you’d do differently with more time, ~30 sec. Speak naturally, as if briefing your board directly — strategic clarity and correct numbers matter, verbal polish does not.