Head of Sales

Glasshouse; United States; Hybrid; USD 180,000 - 300,000; Full time

Job summary

GlassHouse is seeking a high-impact VP of Sales to lead our US-based sales team and accelerate revenue for our AI-powered outbound platform. You will coach AEs and SDRs, own the forecast, and partner with Marketing to scale inbound and outbound motions.

This role offers visibility to the executive team and a path toward VP-level leadership. The role requires deep experience selling to SMBs and mid-market in the home services or vertical SaaS space, plus a track record of building scalable

Qualifications

• Must have led a sales team with 4+ quota-carrying reps.
• Front-line coaching with performance feedback.
• Experience building inbound and outbound SDR motions.
• Experience creating sales tools and processes (sequences, playbooks, automations).
• Able to lead by example in demos and negotiations.
• Data-centric with CRM dashboards and forecasting.
• Experience using AI to enhance sales processes.

Responsibilities

• Be the front line for AEs and SDRs with coaching and reviews.
• Provide weekly executive reporting on bookings and funnel performance.
• Own the team’s new-business ARR forecast and path to leadership.
• Drive adherence to sales processes and CRM discipline.
• Help pull deals across the line with key calls and negotiations.
• Lead outbound lead generation and speed-to-lead across motions.

Skills

Sales leadership

Coaching

Inbound & outbound SDR

CRM dashboards

AI in sales

Tools

HubSpot CRM

Salesloft

Outreach

Job description

At GlassHouse, our mission is to help home service businesses WIN. We are helping home service businesses modernize their customer acquisition with outbound tools that drive leads AND revenue. Our customers are driving significant revenue improvements with an all-in-one outbound sales tool that leverages AI sales agents and intelligent targeting.

We are looking for people to join our team who believe in our mission to drive outbound sales motions into industries that have traditionally been forced to rely solely on inbound channels and live or die on Google, Meta, or other lead sources.

Company Values:

• Excellence in Everything - We hold a high bar for our work, our standards, and our outcomes.
• Team before Me - We put the mission and others before ourselves.
• Honesty is the ONLY Policy - We speak with transparency and bring strong perspectives, shared respectfully.

Working Style:

• You want to be part of building the company you can grow with - You’ll have an opportunity to be part of building your ‘dream job’ by helping to create our path to success.
• We WANT to work hard - Our team members find work fulfilling and want to integrate our work as part of our lives.
• You are a lifelong learner - Come here and learn about the home service industry, teach your coworkers new skills, try new things, and help invent the future.
• We LOVE winning - Our success comes from helping our customers win. We celebrate our customers’ success and the wins of our team members.
• We are on a mission that you believe in - Helping transform the way home services find customers and grow their businesses is a BIG goal. Are you in?
• We push ourselves and each other to grow and improve - We want to be ‘pleased but never satisfied’ - there’s always room to grow and another mountain to climb.
• Commitment to your career - We are committed to the career growth and success of our teams. We want to help each of them reach their career goals, even those that might take them outside of our company (eventually).

Role & Goal:

• Be the front line for our AEs and SDRs - You are the first line of support for the team: daily coaching, call and deal reviews, answering questions, and clearing roadblocks so reps can sell. Weekly team meetings and 1:1 sessions with each team member.
• Executive Reporting - Forecast management to the executive team as part of your path to Sr. leadership. You will be doing a weekly forecast on new business bookings and upsell based on funnel performance and lead generation.
• Own the team number - You are accountable for the team’s new-business ARR bookings and forecast accuracy. You will not carry a personal quota; you win when the team wins.
• Drive process adherence - Run the team’s weekly operating rhythm and hold everyone to our sales process, activity standards, and CRM (HubSpot) discipline.
• Help pull deals over the line - Partner with AEs on deal strategy, join key calls and negotiations, and help close our most important opportunities.
• Drive outbound lead generation - Make sure the team consistently self-sources pipeline, protect prospecting time, and measure and improve outbound results.
• Lead our inbound and outbound SDR motion - Own speed-to-lead, qualification, event follow-up, and outbound cadences so every good lead turns into a held meeting.
• Build SDR and AE tools and processes - Create the sequences, scripts, playbooks, workflows, and automations that make reps more productive, using AI wherever it helps.
• Run the team on data - Build and use CRM dashboards and reports to manage pipeline, activity, conversion, and forecast, and turn the numbers into action.
• Hire and onboard new team members - Recruit, interview, onboard, and ramp new AEs and SDRs, and help each rep build a career path at GlassHouse.
• Partner with Marketing on events - Marketing owns our event strategy; you bring the sales perspective, staff the booth, and make sure every event lead gets fast, disciplined follow-up.
• Partner with Marketing on partnerships - Marketing owns our partner program; you help shape it, support partner relationships, and work partner-sourced opportunities.
• Promote our company culture - Model our values, celebrate wins, and keep the team energized, accountable, and focused on helping customers win.
• Partner across GlassHouse - Work with Customer Success on clean handoffs and retention, and with Product to share what we hear in the market.
• Reporting and growth path - This role reports to our CEO, with a path to VP of Sales and a seat on the executive team.
• Remote Work with/ Hybrid Opportunity - We are a remote team with a hybrid office structure for Nashville area team members.
• Participate in weekly team meetings and trainings - These are generally at 9 am or 3 pm CT but may vary based on events and team availability. Lead and participate in these sessions to keep a culture of constant learning and development.
• Some (but limited) travel - Tradeshow and industry event attendance, plus occasional travel to support key deals, may be required. Attend and engage during 2 annual team meetings. These are generally 3 days.

About You:

• The “must haves”
• Mission and Value alignment
• You’ve led a sales team - You have directly managed 4+ quota-carrying reps (AEs and/or SDRs) and consistently delivered team targets.
• You’re a front-line coach - You get results by making reps better, through call reviews, role-play, deal coaching, and honest feedback.
• You know inbound and outbound SDR - You have built or run both inbound and outbound SDR motions and know what good looks like for each.
• You’ve built SDR and AE tools and processes - You have created the sequences, playbooks, workflows, and automations a sales team runs on. Using AI to build them is a big plus.
• You can lead by example - You are credible in front of business owners and executives, and comfortable stepping into a demo or negotiation to help close a deal.
• You’re very data-centric - You are comfortable building CRM reports and dashboards (HubSpot preferred), managing a forecast, and making decisions from the numbers.
• You’re AI and software savvy - You use AI tools in your daily work, pick up new software fast, and look for ways to automate and improve how the team works.
• We are only hiring in Mountain, Central, or Eastern time zones to keep our team close to our home office hours in Nashville.
• The “nice to haves”
• Nashville, TN area proximity is nice but not required
• Experience at a startup or scale-up growing from $5M to $20M in ARR
• Home services, franchise, or multi-location / PE-backed business experience
• Vertical SaaS experience selling to SMBs and Mid-market
• Familiar with home service software like CRMs, FSMs or other sales platforms
• Outbound sales/marketing tools experience - ZoomInfo, Outreach, Salesloft, Apollo, Salesforce, Hubspot, etc...