About this role.
Anagram is hiring a Head of Sales to lead and scale a high-velocity SMB and mid-market SaaS sales organization for its eye-care insurance billing platform. The role owns revenue performance, forecasting, pipeline health, sales-process improvement, and the development of SDRs and Account Executives. This hands-on player-coach leader will recruit, onboard, and ramp talent while partnering with Marketing and RevOps on lead quality, reporting, and operational efficiency. Strong experience in startup sales leadership, HubSpot discipline, shorter sales cycles, and healthcare or revenue-cycle workflows is preferred.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I begin by diagnosing funnel conversion, activity quality, ramp performance, and pipeline coverage by segment and rep. I then establish a focused operating cadence of call reviews, deal coaching, clear stage definitions, and weekly metric reviews, while addressing enablement or process gaps. This creates measurable accountability without losing sight of rep development.
I use standardized CRM stages with objective exit criteria, inspect the largest and highest-risk opportunities, and compare rep commits with historical conversion and sales-cycle data. I review pipeline coverage, aging, next steps, and close-plan quality on a recurring cadence. Forecast accuracy improves when leaders challenge assumptions early and maintain strong CRM hygiene.
I would isolate whether the issue is top-of-funnel quality, discovery, qualification, value articulation, objection handling, or closing execution. After reviewing calls and deal data, I would agree on one or two observable behavior changes, provide targeted practice and live coaching, and set short-term leading indicators. I would monitor progress closely while making expectations and support explicit.
I hire against a structured scorecard that tests sales fundamentals, coachability, ownership, and fit for the target customer and sales motion. For onboarding, I define product and market milestones, role-play certification, activity expectations, and progressively larger pipeline and revenue targets. Frequent manager check-ins and early call feedback help new hires become productive faster.
I would align on shared definitions for qualified leads, conversion benchmarks, attribution, routing, and feedback loops from sales to marketing. With RevOps, I would prioritize reliable funnel reporting, CRM stage discipline, automation, and actionable dashboards. The goal is to improve lead quality, speed-to-lead, conversion rates, and forecast confidence across the full revenue funnel.
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.
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