Write a GTM plan

Ledgerly Payroll: Go-to-Market Plan (launch 3 November)

The short version

Payroll is an add-on for people who already use Ledgerly, so the launch should be aimed at our existing customers. The draft plan spends most of its effort on new prospects and press, and it uses the headline that lost our own test. I'd make three changes:

• Focus on the customers with the most painful problem.
• Lead with the message that tripled conversion in beta.
• Measure customers actually running payroll and still running it, not launch-week buzz.

1. Who we go after first

Primary: customers with 5–25 employees who run payroll in a spreadsheet or through their accountant. That's 2,170 customers.

• They have the highest penalty rates: 19% for spreadsheet users and 23% for accountant-run payroll, against 4–7% everywhere else.
• They have enough employees to matter. At roughly 12 staff, a customer is worth about $72 a month.
• The calls describe this group exactly: the bakery's $1,400 penalty, the plumber's "scared of getting it wrong", the physio who'd "move tomorrow", and the landscaper paying $180 a month for mistakes.

Second wave: customers with 5–25 employees on another payroll tool (1,210), plus the 460 with 26–50 employees. They're fairly satisfied (5–7% penalties), and switching mid-year "sounds like a nightmare." We should approach them ahead of the next tax-year start, with a migration offer. Until then we just let them know payroll exists.

Not a focus: customers with 1–4 employees (4,160). They have low pain ("a spreadsheet's fine", "annoying, but free") and low revenue per customer. They can find payroll in the product without us pushing it.

2. What we say

The lead message is penalties and accuracy, not speed. In the beta, "Never get a payroll penalty again" won clearly over the speed headline:

That's about three times as many customers running payroll, on comparable traffic of around 4,200 visits each. "Run payroll in minutes" is the losing message, and the calls explain why: "Time isn't the issue."

One important caveat: Legal must approve the penalty claim before we use it. "Never get a penalty again" is a promise. Penalties can still happen if a customer enters bad data or doesn't fund payroll on time. We have two options:

• Back the promise: for example, "If a filing we're responsible for is late or wrong, we pay the penalty." This would be the strongest version, if Finance and Legal agree.
• Soften the wording: for example, "Payroll filed correctly and on time, automatically." We would then re-test this against the winning headline in the first two weeks, because softening may reduce its effect.

Supporting points: - For accountant-run customers: "$6 per employee. For 6 staff, that's $36 a month, not $180." - For everyone: it already lives inside your books, so there's no re-entering data. This is a supporting point, not the headline.

Drop "the first Financial Operating System for small business." No customer has asked for this, it's hard to substantiate, and it says nothing about payroll.

3. Channels

Budget: move the $60,000 away from paid ads to new prospects. New prospects would have to buy accounting before they can buy payroll, so that spend works against our focus. I'd use roughly: - $25,000 for assisted setup staffing and onboarding. - $5,000 for content and the webinar. - The rest held back until December, then released only if setup completion proves to be the bottleneck.

4. How we'll know it's working (November to January)

The main goal is customers who have run at least two payroll cycles. Signing up isn't enough; running payroll repeatedly is what matters.

Check-ins: - Weekly: track the funnel by segment. - Week 2: read the headline re-test, if Legal changes the claim. - End of December: go/no-go on the held-back budget and on starting the switching campaign for customers on other payroll tools.

Caveats

• The beta participants opted in, so real launch conversion will probably be lower than the beta numbers.
• Penalty rates are self-reported.
• The 220 target is a starting estimate, not a forecast. We should revise it after the first month of real data.

To: Executive Team & Head of Marketing From: PM, Ledgerly Payroll Date: October 18 Subject: Revised GTM Plan: Ledgerly Payroll Launch (3 November)

The draft marketing plan targets a generic market with high-level branding. That’s a mistake. We are launching an add-on to an existing base of 8,000 accounting customers. Our unfair advantage isn't that we're a "Financial Operating System"—it's that we already hold their financial data.

We need to scrap the broad acquisition play for November, refocus entirely on our existing base, and lead with our strongest asset: penalty anxiety and accuracy, not speed.

Here are the critical changes I am making to our launch plan.

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1. Who We Go After First (The Wedge)

The data and customer calls tell a clear story.

• Ignore: The 1-4 employee segment doing payroll in spreadsheets (Retail shop: "Annoying, but free"). They don't feel enough pain to switch or pay $6/mo.
• Ignore: Mid-year switchers currently using dedicated payroll tools (Café group: "Switching sounds like a nightmare").
• Target (Our Wedge): Small businesses with 5–25 employees who currently rely on an accountant or a spreadsheet, and are bleeding money/stress on penalties.

Look at the data: 5–25 employee businesses using accountants or spreadsheets suffer 19% to 23% penalty rates annually. Furthermore, customer calls highlight deep resentment toward accountant-driven payroll failures ($1,400 fines, $180/mo fees for mistakes).

We will segment our 8,000 customers on Day 1 and suppress micro-businesses (1-4) from our primary payroll marketing to protect email reputation and conversion relevance.

2. What We Say to Them (The Message)

Marketing’s draft leads with: "Run payroll in minutes."

Our beta test proved this is the wrong hook. Look at the `betaheadlinetest.csv` data: * "Run payroll in minutes..." generated only 38 completed payrolls. * "Never get a payroll penalty again" generated 117 completed payrolls (more than 3x the activation rate).

Time isn't the primary enemy; fear is (Plumbing firm: "I'm scared of getting it wrong. The tax office letter was the worst week of my year").

Our Core Value Proposition: “Keep payroll inside Ledgerly. Zero manual data entry from your books, guaranteed accurate tax calculations, or we cover the penalty.” (Note: We should seriously explore a penalty-reimbursement guarantee as a killer differentiator).

3. Through Which Channels

We are shifting $50,000 of the proposed November budget away from broad paid social/search targeting cold prospects. Acquiring cold payroll customers is expensive and slow; cross-selling our 8,000 warm customers is high-margin.

• Channel 1: Targeted In-App Real Estate (Nov 3): Replace the generic banner with a dynamic state. If the user has 5–25 employees and uses an accountant/spreadsheet, show the "Never get a payroll penalty again" headline.
• Channel 2: Founder/PM Email Campaign (Nov 4–10): A direct, non-marketing-sounding email sent from me (PM) and the CEO to the 5–25 segment. Focus on the hidden costs of accountant errors and spreadsheet slip-ups. Include a 1-click "Import my data" preview.
• Channel 3: The "Fire Your Accountant's Payroll Bill" Playbook: A targeted retargeting campaign (using the remaining $10k of paid budget) aimed strictly at custom matched lists of our 5-25 employee segment, highlighting how much they can save by bringing payroll into Ledgerly alongside their bookkeeping.

4. How We’ll Measure Success (Months 1–3)

Marketing’s draft relies on vanity metrics: press mentions and launch-week sign-ups. We care about retention and activation. Ledgerly Payroll is priced at $6/employee/month; a sign-up that doesn’t run payroll is worthless.

Over the next three months, we will track four strict OKRs:

• Month 1 (Launch & Activation):
• Metric: 500 active payroll accounts set up from the 5–25 employee segment.
• Guardrail Metric: Zero critical calculation support tickets in the first 14 days. Accuracy is our brand promise; a buggy launch kills trust permanently.
• Month 2 (Expansion & Accountant Displacement):
• Metric: 30% of activated users migrating away from their external accountant/spreadsheet for payroll.
• Metric: Average team size of adopting accounts sits solidly in the 8–15 employee range (validating our wedge).
• Month 3 (Monetization & Retention):
• Metric: $15,000 in recurring monthly add-on revenue (MRR).
• Metric: 95% month-two retention for payroll runners (proving they didn't just test it for a month, but integrated it into their operations).

Summary of Changes

We are abandoning the "Financial Operating System" fluff and the broad acquisition spend. On November 3, we laser-focus on our 5–25 employee segment with a message built on fear-relief and accuracy, driving them straight into a high-converting in-app flow.

Ledgerly Payroll: go-to-market plan

What I'd change in Marketing's draft

Who we go after first

Wave 1 (3 Nov): customers with 5–25 employees who run payroll via spreadsheet (690) or an accountant (1,480). That is 2,170 customers, 27% of the base.

• They have the pain. 19% (spreadsheet) and 23% (accountant) got a payroll penalty notice last year, versus 4–6% for businesses with 1–4 staff and 5–7% for those already on a payroll tool.
• They have the money. At $6 per employee, a 12-person business pays about $72 a month, against the $180 a month one landscaper pays their accountant.
• The calls match the data. The bakery, plumber, physio, landscaper and dental practice all describe fear of mistakes, not lack of time.

Not now: - 1–4 employees (4,160 customers): The spreadsheet is "fine" and "free," and only 4–6% were penalized. Leave payroll available in the product but don't push it. - Other-tool users (1,670 customers): Penalty rates are low (5–7%), and switching mid-year "sounds like a nightmare." Revisit at the start of the next tax year with a migration offer.

What we say

The beta test was randomized. "Never get a payroll penalty again" beat "Run payroll in minutes" on setup starts (6.4% vs 2.2% of visits) and on first payroll runs (2.8% vs 0.9%), about 3x on both. Once people started, completion was similar (44% vs 41%), so the headline drives the decision to begin and the product handles the rest.

Core message: "Payroll filed right and on time, so the tax office letter never arrives."

• Spreadsheet owners: "A spreadsheet won't tell you when you've got it wrong."
• Accountant-run: "Stop paying $180 a month to worry about it." Use this to speak to cost and control without attacking accountants. Offer a way to invite their accountant in as a reviewer.

Accuracy promise: The dental practice said, "If you can promise it's right, I'm in." I'd like to offer a penalty-cover guarantee for errors caused by our software. Legal and Finance must approve it by 24 Oct. If they won't, the copy becomes "filed right and on time, with support to fix problems." We should not promise "never" without backing it. The beta headline did well, but a claim we can't stand behind creates risk.

Channels

1. Targeted in-app card and email to the Wave 1 list only, using the winning headline. This is the main channel, and it costs almost nothing.
2. Personal outreach from Customer Success to Wave 1 customers who told us they got a penalty notice (about 470 people by my estimate from the survey rates). Offer a 20-minute guided setup.
3. Webinar, reframed: "Penalty-proof your payroll" with a live setup walkthrough. Run it in launch week and again in week 4, since the second session catches people who weren't ready the first time.
4. Press: one plain release ("Ledgerly adds payroll, $6 per employee"), with no category claim. Follow with customer stories once we have them.
5. Paid: none to new prospects in November (see Budget).

Budget (the $60k)

• ~$15k: guided setup and migration help (contractor or CS time).
• ~$10k: webinars, email production, and case-study content.
• ~$35k: held until the January gate. If Wave 1 works, spend it on search ads for "payroll penalty" intent, aimed at businesses that would adopt accounting and payroll together.

How we'll know it's working (3 months)

Primary metric: paying accounts that have run at least two payrolls. This replaces sign-ups, press mentions and launch-week anything.

Targets (to be recalibrated after week 2, since the beta is my only baseline): - Month 1: at least 5% of Wave 1 has started setup. At least 45% of those run a first payroll, matching beta's 44%. - End of January: about 250 Wave 1 accounts running payroll (~11% of the segment). I'm assuming a 10-person average, which implies roughly $15k MRR. I'll replace that assumption with real headcount data. - Retention: at least 85% of those accounts run payroll in three consecutive cycles.

Guardrails (any breach pauses expansion): - Payroll errors or penalties caused by us: zero tolerance, reviewed weekly. - Support tickets per payroll run. - Churn of the core accounting subscription, which must not rise among adopters.

Measuring real impact: Hold out a random 10% of Wave 1 from all promotion. If adopters in the promoted group don't clearly exceed the holdout, we're only capturing people who would have found payroll anyway.

Decision gates: - Mid-December: If setup-to-first-payroll is below 35%, fix onboarding before pushing further. - Mid-January: If Wave 1 is at or above target and no guardrail is breached, release the held budget and start Wave 2 (other-tool users, ahead of the tax-year switch window). If it's below target, interview non-adopters before spending anything.

Caveats

• Penalty rates are self-reported, and the eight calls are anecdotes.
• Beta customers may be more enthusiastic than the base.
• I haven't seen average headcount per segment, so the revenue estimates are rough.