Sales Development Representative – Stayd
Full-time | Remote (US-Based)
Reports to: Chief Revenue Officer, Stayd
Base: $50,000–$55,000 | OTE: $85,000–$90,000

About Stayd

Stay'd is a consortium of best-in-class short-term rental management companies building one unified brand across multiple US markets. We are building a centralized sales engine that powers organic growth across every brand in the portfolio. This is a fast, hungry culture. We move quickly, we drop our egos, and we win as a team.

Our Core Values

These are not posters on a wall. These are how we operate every day, and how we hire.

• Best in Class. We are not building average. Everything we touch is built to be the best in the industry.
• Solution Oriented. Problems are opportunities. Bring answers, not just questions.
• Move Fast. Speed wins. We ship, we test, we iterate. We don't sit on decisions.
• Drop the Ego. The best idea wins. We sacrifice for the group. We respect each other.

The Role

You'll sit at the holdco level and feed qualified leads into the Account Executives and General Managers at our brand companies. You own the top of the funnel: cold outreach, lead qualification, fast inbound response, and long-term nurture of leads that didn't close the first time. You are not closing deals. You are filling pipelines and making sure no lead slips through the cracks. One SDR typically supports 2 to 3 brands. You will learn those markets cold.

What You'll Do

• Work assigned lead lists (500+ cold contacts per cycle) with consistent weekly outreach quotas.
• Respond to inbound MQLs within minutes. Qualify and book appointments directly onto AE and GM
• calendars.
• Run a structured 4-month sales cycle on cold leads with defined touchpoints, reach-outs, and call
• cadences.
• Hand off qualified leads to brand-level closers with full context (pass-off call plus CRM notes).
• Re-engage lost or stalled leads through a 6-month nurture sequence.
• Keep HubSpot clean and current. Every contact, every stage, every note.
• Attend monthly all-hands sales meetings and contribute scorecard data.
• Use call intelligence tools (Granola, Gong) to sharpen reps and share what's working across brands.

What We're Tracking

• Leads qualified per month
• Contacts per rep per month
• Leads moved to next stage
• CAC and profitability per rep
• Sales-driven churn (deals you booked that stick through onboarding)

Who You Are

• AI-native or AI-curious. Required. You already use AI tools daily and you're hungry to learn more. You don't see AI as a threat. You see it as the unfair advantage that lets you outwork reps who refuse to adopt it.
• Builder mindset. You want to help us design and build AI solutions that aid sales development. Workflows, agents, automations, prompts, dashboards. If you see a manual process, you want to automate it.
• Phone-first. Not afraid to dial. Strong in the first 30 seconds of a cold call.
• Sharp on objection handling and coachable.
• Organized. CRM-fluent. HubSpot experience is a strong plus.
• Hungry, competitive, and professional. You sound like someone an owner would want to do business with.
• Bias toward action. You move fast and figure it out.
• Drop the ego. The best idea wins. You take feedback and apply it the same day.
• US-based. This is a relational industry. We hire people, not outsourced shops.

Compensation

Base: $50,000 to $55,000

OTE: $85,000 to $90,000

Reports To

Chief Revenue Officer, Stayd