Founding Go-to-Market Associate

Colombo (hybrid) · Full-time · USD 200-400/month (LKR 66,000-132,000/month) + share options after confirmation

Own outbound sales to 3,000+ short-term property management companies in the US and UK, and grow into the person who runs our entire go-to-market: sales, client onboarding, and marketing.

About us

Boring Host is building a new hospitality platform: one that doesn't just help guests find homes, but actually operates them with AI agents. Our first wedge is short-term rental property managers, replacing their fragmented stack across guest messages, tasks, cleaners, maintenance, vendors, and owner updates with agents that run operations end-to-end.

In six months we've grown to 640 listings, growing ~15% month on month, and we're selling to short-term property managers with 30-500 listings in a global market of 400M units.

The role

Your #1 job, the thing you'll be measured on, is booking qualified meetings. We have a researched list of 3,000 ideal-fit property management accounts, with 30-500 listings each, across the US and UK.

You own working that list:

• Cold calls, cold email sequences, and LinkedIn outreach. You'll run all three channels.

• Qualify prospects and book meetings for the founder to close.

• Keep the pipeline clean: every account tracked, every follow-up on time.

• Use AI tools for research, personalization, and drafting. We work AI-native, and you'll learn to make these tools do the heavy lifting.

As you prove yourself on outbound, the role widens:

• Client-facing work: sit in on onboarding for new US/UK clients, help configure the product for them, and grow into managing those accounts day-to-day.

• Sales content: turn client wins into case studies and business cases that make the next sale easier.

Within a year, the goal is that you've gone from working a call list to owning real client relationships with companies in New York, London, and everywhere in between, the kind of commercial experience that normally takes a decade and a foreign posting to get, built from a desk in Colombo.

Hours & location

• Office 3 days a week: Monday, Wednesday, and Friday at 14 Sir Baron Jayathilake Mawatha, Colombo 00100, where you'll have a dedicated co-working desk.

• Outbound hours follow the customer's clock, not ours: UK mornings line up with our afternoon, US mornings with our evening. Expect a split schedule on calling days rather than 9-to-5. We'll shape it together, but evening availability is part of this job.

Who we're looking for

• Excellent spoken and written English: you'll be on the phone with American and British business owners daily; this is non-negotiable.

• Fearless on the phone: rejection doesn't dent you, and you're back on the next dial.

• Organized to a fault: 3,000 accounts only works if the follow-up system never drops a thread.

• Curious about AI tools: you are quick to adopt them.

• Hungry to build a career in tech sales and go-to-market: no specific degree or experience required. We care what you can do, not what's on paper.

Compensation & perks

• USD 200-400/month (LKR 66,000-132,000/month), depending on experience, reviewed at 6 months, with a 6-month probation period

• On confirmation after probation: a share option grant from our employee pool, with details in the offer letter

• Dedicated AI tooling: your own Claude Code and Codex Pro subscriptions, about USD 200/month value, for work and personal use

• Dedicated desk in central Colombo, direct daily work with the founder, and first-hire ownership of everything go-to-market

How we hire

Our process is designed to see how you actually sell, not how you interview, and it moves fast: about three weeks from application to offer.

• Application: we review your CV or LinkedIn and your short cold email pitch introducing Boring Host AI to a short term property manager. We are looking for clear writing, sharp positioning, and signs that you understand how to get attention without sounding generic.

• Screening call: a 20-minute conversation in English about you, how you work, why this role, and what kind of sales or customer-facing work gives you energy.

• Mock cold call: a 30-minute role-play where we act as a US or UK property manager and you pitch Boring Host AI. We are grading listening, confidence, recovery, and objection handling, not perfection.

• Paid trial week: you work a small slice of the real account list with real tools, paid regardless of outcome. We look at outreach discipline, follow-up quality, CRM hygiene, and learning speed.

• Decision & offer: within days of the trial ending, we make a call. If it is a yes, the offer includes salary, probation terms, option grant, perks, and start date in writing.

To apply, complete this form with your CV or LinkedIn and email your cold email pitch to [email protected].