Growth Engineer — Sidepocket
Location: San Francisco Bay Area (remote first, occasional in-person meetings)
Type: Full-time
Reports to: COO
Compensation: ~$92K base at hire, with a raise upon our fundraise — plus equity in the form of early-stage founder shares
About Sidepocket
Retirement on autopilot for the self-employed.
22.6 million Americans file self-employment taxes, and only 4.2% claim any retirement deduction. That leaves roughly 21.6 million profitable operators sending money straight to the IRS that they could be sheltering — not because they can't afford to save, but because no one has told them how, and no product has made it automatic.
Sidepocket closes that gap. Our patent-pending Contribution Intelligence Engine™ reads a self-employed person's real bank data, handles the variable-income math, and tells them exactly how much they can safely contribute to a SEP-IRA (and soon Solo 401(k), HSA, and more) any month of the year — then executes, verifies, invests, and reconciles it in a closed loop. Connect your bank, answer a few questions, get your safe contribution number in 7 minutes.
We're arriving at the exact moment the market is exploding: full-time independents in the U.S. doubled from 13.6M to 27.7M between 2020 and 2024, and 580,000+ laid-off tech workers are forming LLCs and consulting practices instead of going back to payroll. These are $150K–$400K earners who just lost their 401(k) match and have no product built for them. We're first to that market, and we intend to stay first.
We're a small, early-stage, SEC-registered team, pre-product-market-fit, with a detailed 200-page go-to-market plan and roughly $200K to execute it. We're looking for the person who turns that plan into 1,000 paying customers and a fundraise.
The Role
You will own go-to-market. Full stop.
The plan exists and it is specific — staged rollout, named channels, named tools, defined kill criteria, unit-economics targets. What it needs is an operator who can run all of it: build the CPA partnership channel, stand up direct acquisition, ship two Product Hunt launches, run the affiliate and referral programs, drive organic community growth, own attribution, and get us to the metrics that make us VC-viable. You'll do this hands-on with the founder and one part-time content/outreach partner, then help hire the team once the model is proven.
This is a zero-to-one job. Early on, everyone does everything — including walking a prospect through signup and doing concierge onboarding on the spot. If "do things that don't scale" sounds like a burden rather than the whole point, this isn't the role.
What you'll own
CPA partnership channel (the validation bridge). CPAs are our highest-trust, highest-confidence acquisition source and the way we validate contribution automation under real tax scrutiny. You'll run partner development end to end: outreach, pitch, onboarding, enablement collateral, co-branded landing pages, and the referral-fee relationships. Target: partners referring 4–8 qualified clients/month at steady state.
Direct acquisition (the volume engine). Own the two-prong motion — precision for high earners ($300K+ where our product is the optimal fit) and speed-and-simplicity for the underserved $40K–$100K segment going from $0 saved to something. This spans cold email infrastructure (Instantly, dedicated domains, warmup), LinkedIn outbound (LinkedHelper, Apollo enrichment), and paid ads across Meta, Google, LinkedIn, and Reddit — activated after organic proof thresholds are met, not before.
Launches & top-of-funnel. Ship both Product Hunt launches — the free Tax Leak Calculator™ first, then the full product — plus webinars and workshops. Own the free-tool-as-top-of-funnel strategy and the nurture flows (Beehiiv) that convert lookers into Starter and Tactical subscribers.
Affiliate, referral & organic. Stand up the affiliate program (Awin, Affiliately) and client-to-client referral loop, and drive authentic organic growth in the communities where our ICP already lives — Reddit especially, which cannot be outsourced and requires a real voice and real karma.
Attribution & the numbers. Own the source of truth (PostHog + Stripe + HubSpot). Keep identity-resolution match rate above 90%, unknown attribution below 15%, and every channel's CAC honest. You'll live in the Success Metrics Dashboard and act on the kill/scale criteria without being told to.
The fundraise story. Everything above ladders up to Month 7+: get to consistent growth, proven unit economics, and evidence of a large market that loves the product — then help tell that story to investors.
Targets you'll be measured against
- ~1,000 paying customers and ~$35K MRR by Month 6 (trajectory to $52K)
- Blended CAC under ~$140, LTV:CAC above 3:1
- Free-to-paid conversion above 15%, monthly net churn under 7%
- Activation above 50%, Month-6 retention above 65%
- Time-to-value under 7 minutes held sacred
Who you are
- 5+ years in growth / GTM / demand gen, with real zero-to-one experience. You've taken something from no traction to a repeatable acquisition motion, ideally at least once as an early or founding hire.
- Full-stack operator, not a manager of operators. You write the cold email, brief the content, read the PostHog funnel, and pick up the phone with a CPA — all in the same week. You're comfortable being the whole growth team before you build one.
- Fluent in both partnerships and performance. You can nurture a relationship-driven B2B2C channel and run disciplined paid acquisition. Most people are good at one; we need both.
- Numbers-native. You instrument before you spend, you know the difference between last-touch and view-through, and you'll shut off a channel that's missing its CAC target without being sentimental about it.
- AI-forward. Our plan runs on lean automation — Claude agents for prospect scoring and weekly reporting, Zapier orchestration, AI-assisted content and ad creative. You should already be building this way, using leverage instead of headcount.
- Comfortable in a regulated environment. We're an SEC-registered investment adviser. Marketing claims, testimonials, and performance language all live under the SEC Marketing Rule. You don't need to be a compliance expert, but you need the temperament to market boldly and stay inside the lines.
- Bay Area-based and here in person. This is built shoulder-to-shoulder with the founder in the early months.
Bonus points
- Fintech, wealthtech, tax, or accounting background
- Experience selling to or through CPAs, financial advisors, or accountants
- Prior Product Hunt launch you drove
- You've sold to freelancers, consultants, or the self-employed and understand how they actually buy — emotion first, facts second
- SEO / content-led growth chops
How we work
We narrow before we widen. One customer type, one product, executed perfectly, before we expand. We validate before we scale — ads accelerate growth, they don't create it. We build contingencies because we expect at least one thing to go wrong. And at this stage, the founder sells, the whole team onboards, and the first 100 customers are the hardest and the most important. If that's the kind of intensity you want, we should talk.
- Sidepocket is an equal opportunity employer. We evaluate all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic.
