Anagram

Head of Sales

USA, United States full-time Mid Salary not listed
full-time Mid level Technology & IT Curated
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About the role

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.

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Mid
Technology & IT CRM Data Analysis Remote Collaboration Sales Mid level full-time

Likely questions

  1. Tell us about work you have done that is close to the Head of Sales role.
  2. How would you approach your first 30 days at Anagram?
  3. Which of CRM, Data Analysis and Remote Collaboration have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with CRM, Data Analysis and Remote Collaboration.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Head of Sales role because I can bring practical experience in CRM, Data Analysis and Remote Collaboration, learn the team quickly, and contribute to the outcomes Anagram needs from this hire.

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