Head of Sales

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
Partnership or channel program experience
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...