Remote Head of Sales

Anagram is the ultimate insurance billing platform for eye care providers. Combining instant eligibility and benefit verifications, patient responsibility calculation, claims management, payment posting, and more, Anagram’s all-in-one revenue cycle management solution is designed to save providers time and money, and free doctors to deliver the best care for their patients. Our mission is to simplify insurance, and it’s working: over 2,000 eye care professionals rely on Anagram to manage their insurance billing.

Founded in 2014, Anagram is the largest and fastest-growing insurance billing platform for eye care providers in America and processes hundreds of millions of dollars each year.

About You

You’re a hands-on sales leader who thrives in fast-paced startup environments. You know how to balance strategy with execution and lead from the front, coaching reps, improving processes, and helping the team consistently hit revenue goals.

You believe great sales leadership is about developing people into top performers. You know how to coach reps through direct feedback, call reviews, deal coaching, and skill development, while building a culture of accountability, urgency, and continuous improvement.

You’re comfortable owning team performance, managing pipeline and forecasting, hiring and ramping talent, and helping build a scalable sales organization as the company grows.

What We’re Looking For

• 5–8+ years of SaaS or technology sales experience, with 2–4+ years managing SMB or mid-market sales teams

• Proven experience leading high-velocity, high-volume sales organizations

• Strong coaching and sales development skills across the full sales cycle

• Experience managing SDRs and Account Executives in a startup or high-growth environment

• Track record of improving team performance, quota attainment, and pipeline conversion

• Experience recruiting, hiring, onboarding, and ramping sales talent

• Strong understanding of sales metrics, forecasting, pipeline management, and CRM discipline

• Experience with HubSpot and sales compensation structures preferred

• Highly operational, accountable, and comfortable working cross-functionally

• Ability to operate as a player-coach and help strategically move deals forward

What You’ll Do

• Own team revenue targets and help drive monthly, quarterly, and annual sales goals

• Lead and develop a team of SDRs and Account Executives through hands-on coaching and performance management

• Act as a player-coach by joining strategic deals, reviewing calls, and helping unblock opportunities

• Improve sales process, pipeline velocity, forecasting accuracy, and conversion rates across the funnel

• Recruit, hire, onboard, and ramp high-performing sales talent as the team scales

• Build structure and accountability around CRM hygiene, activity standards, and pipeline management in HubSpot

• Partner with Marketing and RevOps to improve lead quality, reporting, and operational efficiency

• Help refine sales process, compensation plans, and broader go-to-market strategy

• Build a culture of urgency, ownership, execution, and continuous improvement

Preferred

• Experience selling SMB SaaS products with shorter sales cycles

• Background in healthcare, health tech, or practice management software

• Familiarity with insurance, billing, or revenue cycle workflows

• Experience working in an early-stage or high-growth startup environment

• Previous experience as a top-performing Account Executive or sales leader

• Experience building and scaling sales teams from the ground up

Anagram offers employees:

• Industry-leading compensation, including salary and equity ownership

• MacBook, monitor, and all the technologies you need to succeed

• Full Medical & Dental Insurance

• Unlimited PTO

• 401k

• Remote first company

• Fast-paced startup environment

Anagram is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy), sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by applicable law.