Sales Director

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead the sales team and take ownership of Sentinel's sales figures.

• Personally close significant deals and maintain a personal new-ARR target.

• Target property managers who manage approximately 30 to over 1,000 listings.

• Leverage an existing short-term rental network to create opportunities.

• Manage the complete sales cycle from auditing listing performance to offering free trials and converting to paid subscriptions.

• Focus on negotiating tiers, modules, and commitments instead of simply reducing prices.

• Oversee a distributed team of Account Executives in Canada and Europe, along with outsourced SDRs.

• Aim to double the sales team by mid-2027 through effective hiring, onboarding, training, coaching, and replacement as needed.

• Establish territories, quotas, and compensation plans.

• Conduct weekly pipeline reviews, deal inspections, and call coaching sessions.

• Maintain a rolling forecast for the CEO and board of directors.

• Develop Sentinel's sales playbook that outlines target customers, qualification processes, demos, and pricing strategies.

• Enhance the reliability of free-trial conversions.

• Keep HubSpot data current for accurate forecasting.

• Represent Sentinel at events such as VRMA International, DARM, IMN, SCALE, and various regional meetups.

• Cultivate partner and referral relationships.

• Publish, post, and speak to elevate industry visibility.

⛳️ Requirements

• Extensive and active network within the short-term rental industry, including connections with property managers, revenue managers, and operators.

• Over 5 years of experience in B2B sales.

• Minimum of 2 years of experience leading a quota-carrying sales team.

• Recent experience in closing complex, multi-stakeholder deals.

• Willingness to travel frequently.

• Preferred experience in selling software, data, or revenue services in the vacation rental sector.

• Familiarity with revenue management principles such as RevPAR, ADR, occupancy rates, pickup, booking windows, competitive sets, and minimum stay requirements.

• Experience as a first or early sales leader in scaling from initial paying customers to over $5M in ARR is preferred.

• Ability to establish trust with skeptical property managers.

• Capability and readiness to develop an early-stage sales function and processes.

• Willingness to utilize HubSpot for forecasting and pipeline management.

🏝️ Benefits

• Variable compensation ranging from USD $70,000 to $90,000 at target, with additional bonuses for exceeding targets.

• Full variable compensation guaranteed for the first quarter.

• Significant stock option grant.

• Budget provided to attend key industry events.

• Coverage of 100% of individual medical, dental, and vision premiums.

• Life and disability insurance included.

• 401(k) plan with employer matching contributions.

• Paid vacation along with all US national holidays.

• Flexibility to work from home or any location with dependable Wi-Fi and a dedicated workspace.

• Up to 3 days of paid time off for volunteering through Angels Care.