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Wonderly
Marketing & Sales 14h ago

Head of Inside Sales Operations

Wonderly
CanadaCanada
United StatesUnited States
Full-time
$130,000–$250,000 (base + equity)
Senior-Level
VT

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Job Description

Key Skills Required

Master these to land this role

Lead GenerationInside SalesSales RepresentativeSales OperationsAppointment Setting

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You’ll run the day-to-day of our inside sales team, the front line of how our contractors win jobs.

Our team works the leads we generate for our contractor customers, qualifies them fast, and books onsite appointments on the contractor’s behalf. Every lead that goes cold is money our customers lose, and money we lose. Your job is to make sure the team behind those bookings is staffed, trained, and performing every day.

That means:

  • Managing the team: schedules, coverage, weekend rotation, attendance
  • Hiring and onboarding new reps, and getting them productive fast
  • Listening to calls and coaching reps on what to fix
  • Tracking the numbers that matter (speed to lead, contact rate, booking rate, show rate) and acting when they slip
  • Handling performance issues directly, including the hard conversations
  • Keeping the process documented so the team doesn’t depend on any one person
  • Flagging what’s broken in the process so we can fix it, not just work around it

What Makes This Role Different

Most ops manager roles inherit a team that’s already built and a playbook that’s already set.

Here, the team is growing and the playbook is still being written. You’ll shape how the team is run, not just keep it running. If you see a better way to do coverage, coaching, or onboarding, you say it Monday and we’re testing it Wednesday.

You’ll work directly with me and Victoria, who leads Sales Operations, and you’ll see exactly how your decisions affect our customers’ revenue.

Backgrounds That Tend to Work

People from these backgrounds tend to thrive:

  • Running an inside sales or appointment-setting team
  • Team lead or sales floor manager who coached reps every day
  • Sales ops or support ops at a fast-growing company where you managed people, not just dashboards
  • Home services or remodeling companies where you ran the team that booked in-home appointments

Backgrounds we care less about:

  • Managers who have never sold or booked on the phone themselves
  • Ops or reporting roles with no people to manage
  • Account management or customer success with no team of your own

What matters more than the resume:

  • You’ve managed a team and been responsible for its numbers
  • You can listen to a call and know exactly what the rep should have done differently
  • You can have a hard conversation, say what needs to be said, and move on
  • You notice when something’s slipping before it shows up in the numbers
  • You’re organized, and you keep the team organized without being told twice
  • You’re comfortable with ambiguity and fast changes

Expectations:

  • 60–70 hour weeks
  • Coverage that matches when leads come in, including some weekends
  • Real ownership of the team within your first 2 weeks
  • You own the team’s numbers and we’ll review them together regularly
  • The scope evolves constantly. As the team grows, so does the role.

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Wonderly (operating under wonderly.com) is an aggressive, fast-growing AI-driven business operation and automation platform engineered specifically for local service small-and-medium businesses (SMBs) and franchises. Positioned as an all-in-one software-and-agency hybrid, Wonderly provides service industries—such as contracting, remodeling, roofing, power washing, and landscaping—with an end-to-end digital infrastructure traditionally reserved for enterprise franchises. The company's proprietary platform utilizes a vast ecosystem of coordinated AI Agents to completely manage a business's consumer lifecycle, deploying responsive AI website builders, automated Meta and Google Local Services ad campaign setups, and immediate AI phone receptionists that handle live customer qualifications, scheduling, and quote generations within minutes. By consolidating CRM workflows, localized search/AI engine optimization (AEO), VoIP infrastructure, automated billing, and customer review collection into a single interconnected system, Wonderly eliminates the technical friction of managing multi-app subscription bundles. Operating with a high-disruption performance pricing model, Wonderly scales rapid client acquisition pipelines across North America without demanding upfront vendor or agency costs before delivering real, trackable revenue outcomes.

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