Head of Sales (Sr. Manager/Director)

Head Of Sales

Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

We are backed by General Catalyst, Sound Ventures (Ashton Kutcher and Guy Oseary), QED Investors, Google's Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

We're looking for a metrics-driven head of sales who can lead a high-performing team across a fast-paced, high-velocity sales cycle. This role is best suited for people who are passionate about helping small businesses grow, have a track record of sales excellence and are committed to building trusting relationships with our members.

What you'll do:

• Lead from the front by co-selling with your reps.
• Coach and develop a high-performing sales team with clear expectations and consistent development.
• Inspire your team to go above and beyond for our members and for themselves.
• Own team pipeline management and ensure accurate forecasting.
• Partner with marketing on outbound strategy and top-of-funnel growth.
• Improve sales processes and playbooks to support a high-velocity motion using AI.
• Maintain strong reporting hygiene and support reporting needs.

What you'll bring:

• 10+ years in sales with 4+ years direct management experience with high-velocity teams.
• Strong followership and references.
• A record of exceeding targets as both an individual contributor and a manager.
• An "always learning" mentality.
• Experience using AI tools to enhance sales efficiency.
• Clear and confident communication skills.
• Passion for supporting small business owners is a huge plus.

What we offer:

• Remote-friendly environment: Flexibility to work from home while staying connected to the team.
• Health & wellness: $200 quarterly reimbursement to support your well-being.
• Fresh lunch: Provided on in-office days for those in a hybrid schedule.
• Commuter support: $150 monthly reimbursement for transit expenses for those in a hybrid schedule.
• Time off: Flexible PTO plus 14 company holidays.
• Comprehensive coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents.
• Parental leave: 16 weeks fully paid.
• Retirement & ownership: 401k plan plus an equity package.
• Team connection: Quarterly virtual events and an annual in-person summit.