About the role
HouseWhisper is hiring a Director of Operations & Revenue to be the operational backbone of the company's go-to-market function. You will take ambiguous problems and opportunities directly from the CEO and own them end-to-end — define the approach, do the work, and deliver outcomes. This is a hands-on role for someone who acts like an owner, moves quickly across functions, and is as comfortable inside a SQL editor or HubSpot workflow as they are on a customer call.
You will own revenue operations, billing and compliance, customer onboarding at scale, partnerships and integrations, and the analytics layer that leadership and customers both rely on. As HouseWhisper transitions from a pure SaaS subscription model to a hybrid model that includes a transaction-based Leads Platform, you will be central to making the new revenue motion work operationally.
You are not a coordinator. You execute directly when it is faster, and only involve others when necessary.
What you'll do
- Take problems and opportunities from the CEO and own them end-to-end — define the approach, test solutions, and ship something that works without waiting for perfect direction
- Own revenue operations: CRM workflows, lead routing, pipeline visibility, follow-up sequences, and sales process hygiene in HubSpot
- Own transaction-based revenue tracking — reconcile closed deals against the fee model and ensure billing is accurate, timely, and defensible
- Own the pilot-to-scale transition: design repeatable onboarding playbooks for new clients so the CEO is not in the critical path for every account
- Talk to customers directly, identify friction in the onboarding and engagement experience, and fix it before it becomes churn
- Own compliance operations: maintain TCPA, DNC, and A2P 10DLC registrations and stay ahead of regulatory requirements for outbound calling and SMS as the platform scales
- Build and own integrations and partnerships: map and prioritize CRM integrations (Follow Up Boss, Sierra, LionDesk, and others), turn integration conversations into pilots, and pilots into live, supported connections
- Own internal analytics and reporting: lead engagement funnels, call outcomes, conversion by source, pipeline health, and revenue by account — built in SQL and surfaced through Metabase or equivalent
- Own the customer-facing reporting layer: design and deliver dashboards that help clients see ROI from HouseWhisper and make the case for renewal and expansion
- Work with engineering to instrument the right data and ensure reports are accurate, not just fast
- Use AI as a core execution tool — daily, across research, outreach, analysis, and process documentation. When you see a repetitive task, your default question is: can this be automated?
What we're looking for
- 5+ years in RevOps, BizOps, or a hands-on operations leadership role at a B2B SaaS company, ideally including time at an early- or growth-stage startup
- Direct, hands-on experience administering HubSpot (or a comparable CRM): workflows, deal pipelines, sequences, lead routing, and revenue/subscription objects
- Strong SQL skills — comfortable writing non-trivial queries against a production Postgres database and building reporting in Metabase, Looker, or similar
- Experience owning billing operations end-to-end, including subscription billing, invoicing, dunning, and reconciliation across tools like Stripe, Maxio/Chargify, or similar
- Track record of taking ambiguous problems from a founder or executive and turning them into shipped outcomes without needing a defined scope
- Comfort talking to customers directly — running calls, gathering feedback, and translating it into operational changes
- Extremely high attention to detail and a bias toward fixing things yourself rather than delegating
- Excellent written and verbal communication: you can document a process clearly, write a defensible attribution methodology, and explain a tradeoff to leadership in plain language
Nice to have
- Real estate industry experience, especially with agent teams, brokerages, or ISA operations
- Experience with transaction-based or referral-fee revenue models in addition to subscription SaaS
- Familiarity with TCPA, DNC, and A2P 10DLC compliance for SMS and outbound calling
- Experience with CRMs commonly used by real estate agents (Follow Up Boss, Sierra, LionDesk)
- Experience with AI/automation products or conversational AI
What good looks like
- Three months in: onboarding is systematized, compliance is owned, billing and revenue tracking are clean, and customers have a reporting layer they reference
- Twelve months in: the operations layer is a competitive advantage — faster onboarding, cleaner data, accurate transaction-based billing, and a reporting story that accelerates renewals and expansion
Compensation & benefits
- Competitive Compensation
- Stock Options
- Health insurance, Medical, Dental & Vision
- 401k
- Flexible Time Off policy
Our commitment
We're committed to building a diverse and inclusive team and encourage candidates of all backgrounds to apply.
About HouseWhisper
HouseWhisper is an AI-powered assistant that addresses one of the real estate industry's key challenges — streamlining lead management and follow-ups. Founded by former Zillow executives, HouseWhisper acts as a 24/7 virtual teammate, handling administrative tasks such as CRM updates, personalized follow-ups, and scheduling, all through simple interactions. By automating routine work, it allows real estate agents to focus on closing deals and nurturing client relationships. Trusted by agents to increase productivity and efficiency, HouseWhisper empowers professionals to grow their businesses and stay competitive in a fast-paced market.
Pay: $150,000.00 - $175,000.00 per year
Work Location: In person
