Solutions Engineer

Whippy sells a deeply technical product into a non-technical industry. Every serious deal involves an ATS integration, telephony architecture, AI agents, and workflow automation. Today, that technical depth in the sales cycle comes from our founders. One of our largest prospects described why it works: our CTO came in as an engineer giving a solution, not a salesperson giving a pitch. Buyers drop their guard for engineers.

This role exists so that credibility scales beyond the founders. Your mission: make complex Whippy deployments provable in pre-sales and repeatable in post-sales.

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 today is staffing and HR, where we are the category leader, and new verticals are already opening behind it. We serve more than 1,000 customers, with an engineering team larger than the rest of the company combined. Our enterprise pipeline includes multi-hundred-branch companies deploying AI agents across their entire footprint. The deals are here. The person who makes them technically real is you.

How we work

Bootstrapped and profitable, so revenue is the strategy. No task is above or beneath anyone here, including the CEO, who still cold calls, and the CTO, who still runs demos. AI-first in how we work, not just what we sell. Speed over polish. Results over activity.

The job, pre-sales

You design the solution on complex deals: which products, how they connect to the prospect's ATS, what writes back, and what the rollout across branches looks like. You own the technical deep-dive call, the meeting where the prospect brings their IT admin, and you answer definitively. A confident "no, but here is the workaround" builds more trust than a guessed yes.

You carry encyclopedic knowledge of our major integrations. You build prospect-specific sandboxes and working AI agents for proof. You own RFPs and security reviews end-to-end so the AEs stay selling. You travel with the sales team as the technical face of Whippy at industry shows and enterprise on-sites, because the biggest deals are won in rooms, not inboxes.

The demo environment that can never fail is your personal SLA.

The job, post-sales

You design deployment architecture for enterprise accounts and hand healthy, fully documented implementations to Customer Success. You take the technical escalations that go beyond standard support. And you build the pattern library: every solved deployment becomes a documented, reusable playbook, so the next account starts from a pattern instead of a blank page and the whole team levels up on your work.

You also own the feedback loop to engineering: what we lose deals on, what every prospect asks for, where competitors exploit gaps.

Where the line sits

The AE always runs discovery, always runs the first demo, always owns pricing and the close. You never join a first call. You join when a technical evaluator is joining the next meeting, when the solution needs custom architecture, when a proof of concept needs building, or when an integration question has stumped the AE twice. If a deal arrives without a completed discovery brief, you send it back. This role is a weapon the AEs deploy, not a crutch they lean on.

What success looks like

• First 30 days: you can run our standard demo solo and have shadowed every active enterprise deal.

• First 90 days: you own the technical calls on live deals and have shipped the first three playbooks in the pattern library.

• Year one: you own the technical motion on every enterprise deal, the pattern library covers our top ten deployment types, and the founders have not run a scoping call in six months.

Who succeeds here

You have been an SE, Solutions Consultant, or senior Implementation Engineer in staffing technology, ATS ecosystems, or CCaaS and business telephony. You do not write production code, but you read API docs fluently, test endpoints without an engineer, and can debug an integration live on a call. You have built or configured AI agents or IVR flows, you can run a technical demo solo under hostile questioning, and you write documentation people actually use. You explain architecture in plain English to a business owner and hold your own with their IT team in the same meeting. You get genuine satisfaction from making the deal work, not from being the hero of the room.

This is not for you if

• You need a solved problem handed to you with a runbook.

• You want to stay behind the scenes. This role is customer-facing every week.

• You see documentation as someone else's job.

• You cannot travel to shows and customer sites.

Why join now

The technical motion that closes our biggest deals currently lives in two founders' heads. You are the person who scales it, owns it, and builds the playbook that everyone after you runs.