All figures are in USD
Our client is a venture backed US B2B SaaS business, founder led and fully remote, selling document software into regulated industries.
The go-to-market was already inbound: a marketing engine booking 30 to 40 demos a month, deal sizes from $1K to $60K with occasional enterprise outliers, and one account executive carrying a quota.
This was the first commercial leadership hire the company had ever made, reporting directly to the Founder/CEO, who had been running sales.
The brief at kick-off asked for someone who could scale from zero to $5M, take over the existing AE and build a larger team.
That requirement kicked off the search for a Head of Sales.
WHAT OUR CLIENT DISCOVERED
They out-earn the salary band allotted for the role.
These are 3 of the people we met in the first phase of the search: HEAD OF SALES
The Quota Machine
$180K base. Target OTE: $350K to $400K, plus around 0.5% equity.
- Founding Head of Sales at an enterprise messaging SaaS.
- Closed $19.6M against a $19M quota in his most recent year, after $9M against $8M the year before.
- Took ARR from roughly $4M to $9M, then to $19.6M. Built a team of 18 AEs and two team leads.
- Net new logos from 32 to more than 70.
- Moved the book off one-year deals, cutting single-year contracts from over 90% to 30%.
- Forecast accuracy within 5% for six consecutive quarters.
- Three exits behind him. Based in Texas.
The Document Workflow Specialist
Previous base $220K. Desired base $200K to $220K. Target OTE: $400K to $500K, plus 0.75% to 2% equity.
- Head of Sales at a compliance software company, reporting to CEOs for more than a decade.
- First US hire at an automation business, where he scaled the American organization to 70 people in about a year.
- Took another company from $8M to $25M ARR.
- Deal range from a $30K mid-market floor to $2M enterprise.
- Six-plus years specializing in document workflow automation, which made him the most on-domain commercial leader in the entire pipeline.
- Based in NYC.
The One Who Closes
$200K base plus bonus and equity. Wanted $210K base and a $300K OTE.
- First sales hire and Head of Account Management at a Series A B2B SaaS.
- Scaled it from $600K to $3.5M ARR, doubling year over year, at 200%+ net dollar retention.
- Personally closed roughly 60% of all company ARR.
- Landed their first $100K client and their first contract worth over $1M.
- Before that, 240% of quota at an AI company, closing a $9M multi-year deal against a $3M target, and a $25M+ territory with five to nine AEs at a large enterprise.
- Based in San Francisco.
WHAT A HEAD OF ACCOUNT MANAGEMENT COSTS
Eight months into the search, the search strategy pivoted away from a Head of Sales, to someone who could take a solo user/customer who signed up through self-serve, reach a senior person at their company, and convert that into a multi-user, multi-year contract.
Different job entirely. The search was rebranded to Head of Account Management.
These are the candidates we presented for that pivot:
The Expansion Builder
$225K OTE on a 60:40 split.
- Head of Account Management at a seed-funded analytics company.
- At a previous employer he built the AM and CSM functions from scratch while company ARR went from around $9M to $18M, with his own team’s share moving from $9M to nearly $14M.
- Took retention from about 70% to over 90% in his first year.
- Team peaked at 13 people across the US and EMEA, with account manager quotas split 75% retention and 25% expansion.
- At a $5M business before that, he did the exact motion this role needed: converting self-serve sign-ups into enterprise contracts.
- Based in Colorado.
The Portfolio Scaler
$250K OTE on an 85:15 split, so roughly a $212K base.
- Head of Customer Success at a Series A legal technology company, headhunted into the role by the CEO.
- Earlier, joined a business at $7M ARR with four or five CSMs and grew the team to 12; after an acquisition she scaled it from 12 to 24 globally in six months, and to 65 over two years.
- By the end her team held a portfolio worth $65M ARR.
- The business sold for seven times.
- Based in Mississippi.
THE HIRE (YAY!)
Offer accepted at a $165K base, with an OTE target of around $225K discussed.
- He had been earning a $150K base with discretionary bonuses and no commission.
- The first ever sales hire at a digital company, hired as Head of Account Management and the most senior commercial person there.
- He built a team of eight: three account managers, three CSMs and two SDRs.
- The company grew from under $1M to more than $7M ARR across four years, and his account managers drove more than $2M of that through expansion alone.
WHY the client said yes to this candidate:
He had done the exact motion, at the exact stage, in the exact direction they needed to go.
They had a playbook for taking existing users and expanding them, at a company that went from under a $1million to $7million,.
WHY the candidate said yes:
A foundational seat working directly with the founder, a product he thought solved a real problem rather than a nice-to-have, and a genuine remote guarantee.
He had other offers on the table paying more. He took this one.
KEY INSIGHTS:
The title of your intended hire matters.
It determines which community of prospective candidates you are going to invest your time engaging with.
The Heads of Sales we screened in the first wave were asking for $350K to $500K OTE. The Heads of Account Management we screened later were asking $210K to $250K. Same seniority, same stage of company, same B2B SaaS.
Which market you belong in is decided by where your revenue actually comes from, not by how you would like to describe it.
This company had a marketing engine booking 30 to 40 demos a month and a self-serve product bringing in individual users. There was no outbound problem to solve. Hiring a leader whose entire value is building an outbound machine would have cost nearly twice as much and pointed that machine at a pipeline that was already full.
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