Head of Marketing

Head of Marketing at Whippy

Remote, United States | Full time | Reports to the CEO

Bonus points if you are in or near Los Angeles, New York, or Miami: the CEO splits time across all three, and this role works best with regular in person time, working sessions, customer dinners, and trade shows together.

Total Comp: $140,000 to $160,000 OTE ($120,000 to $140,000 base plus variable tied to marketing sourced pipeline), depending on experience and location. Plus meaningful equity in a bootstrapped, profitable company: no investor preference stack ahead of you, no dilution to date.

You are being hired to fire the CEO from his second job.

Whippy grew to 1,000+ customers with almost no marketing team. Pipeline comes from founder led webinars, partner channels, referrals, and customer stories good enough that prospects quote them back to us. Right now the CEO personally directs the website, organizes the events, writes the case studies, and approves every asset. Your job is to take motions that already work, build machines around them, and own a pipeline number the way an AE owns a quota.

Why Whippy

Whippy is the AI native platform for business communication: AI Voice Agents, AI Recruiting, messaging, VoIP, deep integrations, and our own workflow engine in one system. Our customers do not buy software that helps their employees do the work. They buy AI that does the work.

Our deepest market is staffing and HR, where we are the category leader, and new verticals are already opening behind it. We are bootstrapped and profitable, with named, public case studies showing customers saving $1M+ per year. The proof exists. The machine to distribute it does not. That is the problem you are hired to fix.

How we work

Bootstrapped and profitable, so revenue is the strategy, and marketing is measured in pipeline, not impressions. No task is above or beneath anyone here: you will interview customers yourself, write the first draft yourself, and build the campaign yourself. Use AI for leverage: research, repurposing, ops, the grunt work. Never for voice.

The mandate, in priority order

1. Codify our messaging, then enforce it. Your first deliverable: extract our positioning from the founder's webinars, demos, and the language customers use in our case studies, and turn it into one messaging document, positioning, product one liners, proof points, banned phrases, that everything shipped afterward draws from. The messaging exists today; it lives in the founder's head and a dozen slightly different pages. You make it one source of truth.
2. Own the proof engine and enablement. Build the case study library: extract stories from webinar and call recordings, interview the customers, draft in our voice, get approvals, and arm every story as a page, a PDF, a one pager, and clips cut from recordings we already have. Then productize enablement on both sides of the wall: for our sales reps, battlecards against the tools we replace, ROI calculators, and per product one pagers built from our Solutions Engineer's technical documentation; and for our partners, enablement kits for the ATS reps who already recommend us inside their own demos and have never been given a single asset to do it with.
3. Own lifecycle marketing, retargeting, and marketing HubSpot. This is the low hanging fruit and the measurement backbone in one. Audiences we already own and never touch: a thousand customers who hold one product and have never heard about the other five, everyone who demoed and did not close, closed lost deals, and warm site traffic with no retargeting layer. You build the sequences, the new product announcement motion to the base and to dead pipeline, and the retargeting programs. And you own the marketing side of HubSpot, lifecycle stages, campaign tracking, attribution from first visit through demo to close, working alongside our sales ops and web ops resources, so for the first time we can say which motion sourced which dollar.
4. Run the machine around our events. The CEO runs the webinars; he is the talent, you are everything before and after the hour: promotion, registration, partner co promotion, follow up sequences, and extraction, so every webinar becomes case studies, clips, and campaigns within two weeks instead of sitting in a recording. You own the trade show process end to end, pre show meeting booking, booth and collateral, post show sequences, and you run our high touch motions: the customer dinners, the gifts, the executive touches that win enterprise deals and today happen only when the CEO remembers.
5. Build the content function. You own editorial from day one: set the priorities against the messaging doc, then hire the writer or agency you want under you. You inherit a real asset base, a case study library, webinar recordings, and a competitive framework already winning deals, and you decide who produces against it.

Second wave, once the machine runs: paid acquisition on LinkedIn and search tested small against a proof library that can convert it, website conversion surgery page by page, review site presence, AI search optimization, and comparison pages against the tools we replace.

What success looks like

First 30 days: the messaging doc exists and the CEO signed it, you know our six products, three main competitors, and customer stories cold, and the first lifecycle sequence is live.

First 90 days: two new named case studies shipped and armed, and the first cross sell campaign live to the customer base.

First six months: partner enablement kits in the hands of at least two ATS partner teams, and attribution reporting live in HubSpot from visit to close.

Year one: marketing is a predictable pipeline channel with its own number, the proof library covers every product and vertical, trade shows run without the CEO organizing them, and he has not directed a website page, chased a case study approval, or built an event follow up sequence in six months.

Who succeeds here

You have at least 4 years in B2B SaaS marketing where you owned a pipeline number, not an impressions number, ideally at a vertical SaaS company selling to SMB owners and operators. You are a player coach: you build the machine and you run it yourself until it earns headcount. You can show us named case studies you personally got approved and explain how you got each customer to yes. You are hands on in HubSpot: lifecycle stages, campaigns, attribution, not just sending emails from it. You have run a webinar or event to pipeline motion and know your numbers. You write clearly and fast enough that a demanding founder reads your draft and does not reach for the red pen. You have managed at least one person or agency and made the work better. Bonus points if you started in sales or SDR work, because you will be embedded with the sales team and you need their instincts.

This is not for you if

You want a brand role. This is a pipeline role.

You talk strategy more fluently than you talk numbers.

You need an agency and a big budget before anything ships.

You want to manage the work instead of doing the work.

Why join now

The hardest part of marketing is having something true to say. We have customers saving seven figures with named executives on the record, a category lead in AI, partner reps who recommend us unprompted, and a founder who generates demand every time he speaks. What we do not have is the machine that turns all of that into pipeline. You are the machine builder, and you get to build it your way.