Senior Account Executive

Grand Welcome; United States; Remote; USD 90,000 - 150,000; Full time

Benefits offered by this job

Competitive Compensation

Health Coverage

Vision Coverage

Dental Coverage

401k Match

PTO

Equipment Provided

Company Values

Job summary

Grand Welcome is launching a services offering for independent vacation rental managers. As a Senior Account Executive you’ll open conversations, run business reviews, and convert them into signed partners.

You’ll work directly with the CEO to shape the go‑to‑market offer and own pipeline management in HubSpot while leveraging AI tools across the sales cycle. The role is remote in the US, with travel to industry events and conferences.

Qualifications

• Experience selling B2B services to vacation rental managers.
• Fluency in VRM economics: management fees, gross vs net revenue, RevPAR, owner costs.
• Recent experience selling to vacation rental or short-term rental property managers.
• Proven ability to build a pipeline via prospecting and outbound and close new business.
• Strong consultative selling skills: diagnose a business, not just demo a product.
• Existing network of property managers to contact now.
• Hands-on HubSpot: manage contacts, deals, sequences, dashboards.

Responsibilities

• Build and maintain a target list of independent property management companies in our launch markets.
• Run outbound outreach by phone, email, LinkedIn, and in person, using your network and marketing leads.
• Follow up on inbound leads within one business day.
• Lead business reviews with property managers, partnering with the Performance team on analysis.
• Turn reviews into proposals and negotiate to signature within approved pricing.
• Handover signed partners to onboarding and stay involved through go-live.
• Manage your pipeline in HubSpot and log calls, meetings, and deals daily.
• Use AI tools throughout the sales cycle for prospecting, personas, reviews, and call summaries.
• Lead a monthly deep-dive review with the CEO on pipeline results and market feedback.
• Travel for conferences and trade shows, coordinating marketing efforts and campaigns.

Skills

Outbound sales

B2B sales

CRM proficiency

AI tools

Tools

HubSpot

Job description

Grand Welcome operates and supports vacation rental management businesses in 60+ markets across the US. We are launching a services offering for independent vacation rental managers. Partners keep their own brand and independence and choose the services they need from our platform: revenue management, listing optimization, channel management and distribution, fee optimization, PMS configuration and management, owner sales and retention, guest services, and purchasing power.

Every partnership starts with a deep-dive business review that assesses the manager’s business, identifies where it is leaving revenue and margin on the table, and recommends the services that fit.

As Senior Account Executive, you open conversations with independent property managers, lead those business reviews, and turn them into signed partners. You work directly with the CEO and help shape the offer as it goes to market.

Reports to: [ CEO ]Direct reports: NoneLocation: Remote, US

Responsibilities

• Build and maintain a target list of independent property management companies in our launch markets.
• Run outbound outreach by phone, email, LinkedIn, and in person, using your own network and the leads our marketing generates.
• Follow up on every inbound lead within one business day.

Business Reviews & Closing

• Book and lead business reviews with property managers, working with our Partner Performance team on the analysis.
• Turn reviews into proposals and negotiate to signature within approved pricing.
• Hand signed partners to our onboarding team and stay involved through go-live.

HubSpot, Reporting & AI

• Manage your pipeline in HubSpot, our CRM. Log every contact, call, meeting, and deal stage within one business day, with calls and meetings recorded or transcribed where the prospect consents.
• Update and use tasks for follow ups and the Sales Workspace in Hubspot to stay on task with follow ups
• Lead each client from first conversation through signed services agreement, working with the CEO on terms.
• Keep a live pipeline dashboard in HubSpot, available at any time: new leads, reviews booked and held, proposals out, and expected close dates.
• Use AI tools throughout the sales cycle: researching prospects, building client personas, preparing business reviews, and summarizing calls.
• Lead a monthly deep-dive review with the CEO on pipeline, results, and market feedback.

Market Presence & Feedback

• Work with marketing to identify changes or additions needed on website, marketing materials and in content needed for promotion.
• Travel for sales trips, and represent the offering at conferences, industry events, and on LinkedIn.
• Lead and organize the trade shows, including booths, marketing materials, and coordinate corporate attendance.
• Work with our marketing team as one plan: agree on campaign initiatives, target lists and markets, and outreach messaging and sequences, and track which ones turn into business reviews and signed partners.
• Bring back what you hear in the market: objections, competitor offers, and gaps in the offer.

How Performance Is Measured

Performance in this role is measured against targets agreed at the start of the engagement, covering:

• Business reviews booked and held
• Proposals issued
• Partners signed
• Gross margin from signed partners
• Pipeline and HubSpot accuracy

First 90 days: by day 30, target list built and outreach running, and first business reviews booked; by day 60, business reviews held and proposals out; by day 90, first 3 partners signed and a pipeline that will keep signing.

Qualifications

• Experience selling products or services in the vacation rental industry is a must B2B sales.
• Fluency in VRM economics: management fees, gross vs net revenue, RevPAR, owner acquisition costs, owner retention, staffing costs
• Recent experience selling to vacation rental or short-term rental property managers.
• Successful track record of building your own pipeline through prospecting and outbound and closing new business.
• Comfort with a consultative sale: diagnosing a business, not just demoing a product.
• An existing network of property managers you can contact now.
• Hands‑on HubSpot experience: managing contacts, deal pipelines and stages, email sequences, and building your own pipeline dashboards and reports.
• Comfortable using AI tools as part of your sales process.
• Working knowledge of major PMS systems, revenue management, distribution, and guest services preferred.
• Active in VRMA or regional property manager associations preferred.

Working Conditions

• This is a remote position. The role requires travel for sales trips and industry conferences, which may include overnight travel.
• Must be able to work independently and in collaboration with a team in a remote position.
• Schedules vary based on business need and prospect availability across US time zones, so flexibility is expected.
• While performing the duties of this job, the employee is regularly required to talk, hear, and work at a computer for extended periods.

How success is measured

Year‑one signed partners: 20| 5 in the first 90 days

Units under service: 600

First meeting to signature: 60 days or less

Retention at 12 months 90%+

Services per partner: 1 at signing, 2 at 12‑month mark.

Financial targets, including revenue and gross margin per partner, and the compensation tied to them, will be discussed with finalists and set out in the offer and compensation plan.

• Competitive Compensation
• Health, Dental, and Vision Coverages
• 401k with match
• PTO
• All the equipment you’ll need to be successful
• Join a team that truly lives their values

Grand Welcome is proud to be an equal opportunity employer (EEO) to all employees and applicants without regard to race, color, religion, sex, national origin, age, disability, or genetics. Differences are what make us better. We will ensure that all individuals with disabilities are provided appropriate accommodation to participate in the hiring process, perform core job responsibilities, and receive other benefits and privileges of employment. Please contact us to request accommodation.