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# Head of Sales

Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move.

[Apply for this job](#job-application)[View company](https://jobicy.com/company/anagram.md)Share24 Aug 2026Published27Listing views0Application actions23 Sep 2026Apply before  Opportunity details

## About this role.

AI SummaryAnagram 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

5/5EasyHard

### Pace & Pressure

5/5RelaxedFast-paced

### Autonomy Level

5/5GuidedFull ownership

### Communication Load

5/5IndependentCollaborative

AI insightThis is a senior, business-critical leadership position with direct accountability for revenue outcomes, hiring, forecasting, and building scalable operating systems. Success requires both strategic judgment and day-to-day deal, coaching, and performance-management execution in a fast-paced startup.

## Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job medianHighly competitive$270,000US market range$220k–$320k0$352k

AI insightThe disclosed annual compensation range is USD 250,000 to USD 290,000, producing an offer midpoint of USD 270,000. For a US-based Head of Sales at a growth-stage SaaS company, a reasonable market range is approximately USD 220,000 to USD 320,000 annually, though total earnings can vary materially based on variable compensation, equity, team size, and revenue scope.

## Core skills

Skills and capabilities most closely associated with this opportunity.

[SaaS sales leadership](https://jobicy.com/jobs?search_keywords=SaaS%20sales%20leadership.md)[Revenue ownership](https://jobicy.com/jobs?search_keywords=Revenue%20ownership.md)[Sales coaching](https://jobicy.com/jobs?search_keywords=Sales%20coaching.md)[Pipeline management](https://jobicy.com/jobs?search_keywords=Pipeline%20management.md)[Sales forecasting](https://jobicy.com/jobs?search_keywords=Sales%20forecasting.md)[HubSpot CRM](https://jobicy.com/jobs?search_keywords=HubSpot%20CRM.md)[SDR management](https://jobicy.com/jobs?search_keywords=SDR%20management.md)[Account Executive leadership](https://jobicy.com/jobs?search_keywords=Account%20Executive%20leadership.md)[Sales recruiting](https://jobicy.com/jobs?search_keywords=Sales%20recruiting.md)[Go-to-market strategy](https://jobicy.com/jobs?search_keywords=Go-to-market%20strategy.md)

Sample interview questionsHow have you improved performance in a high-velocity sales organization?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.

How do you build an accurate sales forecast?

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.

How would you coach an Account Executive who is active but missing quota?

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.

What is your approach to hiring and ramping sales talent in a startup?

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.

How would you partner with Marketing and RevOps to improve revenue performance?

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

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

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

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Strong coaching and sales development skills across the full sales cycle

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

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

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Experience recruiting, hiring, onboarding, and ramping sales talent

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

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Experience with HubSpot and sales compensation structures preferred

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Highly operational, accountable, and comfortable working cross-functionally

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

What You’ll Do

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

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

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

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

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

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

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

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

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

Preferred

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Experience selling SMB SaaS products with shorter sales cycles

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Background in healthcare, health tech, or practice management software

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Familiarity with insurance, billing, or revenue cycle workflows

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

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

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Experience building and scaling sales teams from the ground up

Anagram offers employees:

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Industry-leading compensation, including salary and equity ownership

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

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Full Medical & Dental Insurance

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Unlimited PTO

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401k

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Remote first company

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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.

Show more

[Apply now >](https://jobicy.com/jobs/151530-head-of-sales.md)

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