Location: Remote (US/Canada) | Department: Sales | Reports To: VP, Revenue
About Cloudwork|PRO
Cloudwork|PRO is changing the way field service is managed. Our marketplace is the fastest, most reliable way for multi-site businesses to find, schedule, and manage independent technicians anywhere in the country, at the click of a button. We've productized what used to take weeks of phone calls and spreadsheets. A Starlink install, a conference room build, a 400-site camera rollout, all sourced, scheduled, and dispatched by expert teams working alongside agentic AI that streamlines and accelerates every step.
We're well funded, growing fast, and constantly releasing new products and platform capabilities. Our customers are the businesses that keep the physical economy running: MSPs and integrators, IoT and smart-building platforms, telecom and UCaaS providers, EV charging networks, healthcare clinic groups, facility-management outsourcers, and national retail and restaurant brands. Every one of them has sites in metros they can't staff, and we're becoming their default field layer.
The Role
You'll own a full-cycle sales motion into our highest-priority customer profiles. That means building named target lists, running AI-assisted outbound, and converting first work orders into expanding, recurring accounts. This is a hunter role on a team where the priority map is data-driven, the triggers are documented, and the product closes fast when the pain is real.
What you'll do
- Own a book of named accounts across our Tier-1 ICPs: regional MSPs and AV/low-voltage integrators, IoT and smart-building deployment platforms, telecom aggregators, UCaaS/VoIP providers, EV charging operators, FM outsourcers, healthcare clinic networks, and multi-site retail/restaurant brands
- Run the full sales cycle: prospecting, discovery, demo, pilot, close, and land-and-expand
- Build and work trigger-based pipelines (PE roll-up announcements, contract wins, rollout programs, funding rounds) using AI-driven outbound and enrichment tooling
- Sell both the marketplace and our productized offers (fixed-scope, one-click installs) as the wedge into new accounts
- Convert first work orders into habitual platform use and own expansion within your accounts
- Feed what you learn back into our ICP scorecards, messaging, and playbooks
What you bring
- 3+ years of full-cycle B2B sales experience selling into one or more of our core buyer types: MSPs/IT channel, SaaS or IoT platforms, telecom/UCaaS, facility services, multi-site retail/healthcare operators, or adjacent field-services markets
- A verifiable track record of meeting and beating quota. You know your numbers and you're proud of them
- Hands-on fluency with AI-driven outbound automation, with tools like Clay, Apollo, Outreach/Salesloft, or AI SDR agents, and a point of view on how AI changes prospecting
- A hunter's mentality: you build your own lists, spot buying triggers early, and open with pain, not features
- Comfort selling to Ops, IT, and field-services leadership from Manager to C-suite
- Startup readiness: you thrive with ambiguity, speed, and a playbook that improves every quarter, often because of your input
Nice to have
- Experience selling marketplaces, labor platforms, or dispatch/field-service software
- Existing relationships in the channel (MSPs, TSDs, telecom agents) or in multi-site operations
- Familiarity with land-and-expand motions and product-led onboarding
Why join
- Well funded and fast growing. Real revenue, real customers, and a market we're defining
- Ever advancing. AI-assisted dispatch and one-click productized installs that make you faster every quarter
- A data-driven GTM. Scored and tiered ICPs, documented triggers, and tested messaging so your time goes where the odds are best
- Competitive base plus uncapped commission, equity, and benefits [details]
Cloudwork|PRO is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
Job Type: Full-time
Pay: $65,000.00 - $150,000.00 per year
Benefits:
- Dental insurance
- Flexible schedule
- Flexible spending account
- Health insurance
- Health savings account
- Life insurance
- Paid time off
- Parental leave
- Referral program
- Vision insurance
Work Location: Remote
