Sales Executive Search
Executive Sales Recruiters
Jackson Square Company is a sales-only search firm placing revenue leadership — Sales Managers through Chief Revenue Officer — for companies hiring their first sales leader or replacing one. We screen leaders on what their teams produced, not on the quota they carried themselves.
Why hiring a sales leader is a different search
Hiring a rep is a question of production. Hiring a sales leader is a question of whether someone can produce through other people, at your stage, inside a scope everyone actually agrees on. Executive sales recruitment fails far more often on those three things than on candidate quality — and none of them are visible on a résumé.
A leader's own quota history is the least useful signal
Almost every candidate can show you a year they beat their number as an individual contributor. That tells you very little about whether they can build a team that hits its number without them personally closing it. The transition from carrying a bag to producing through other people is the hardest one in sales, and plenty of excellent individual contributors get promoted and never make it. The search has to be built around evidence of team output, not personal output.
Stage fit is decisive at leadership level
The person who builds a first repeatable sales process out of nothing — writing the playbook, taking calls themselves, hiring the first four reps — is rarely the person who scales an existing forty-rep organization through layers of management and reporting. And the reverse fails just as often: a leader used to structure, headcount, and enablement support can stall completely when asked to invent all three. Matching the candidate to your stage is not a preference; it is usually the deciding variable.
The scope of the job varies enormously under the same title
One company's VP of Sales owns a rep team and a quota. Another's owns marketing, customer success, partnerships, forecasting to a board, and comp plan design. Same title, entirely different job. Misaligned scope expectations end more leadership hires than skill gaps do — the person accepted one role and arrived to another. Scope has to be written down and agreed before sourcing starts, including what the role explicitly does not own.
Confidentiality changes how the search can be run
When a company is replacing a current sales leader, the search often has to run without the incumbent, the team, or the market knowing it exists. That constrains everything: how candidates are approached, how much can be disclosed early, when references can be taken, and which channels are usable at all. An open search and a confidential search are not the same project, and pretending otherwise is how a replacement search leaks.
The stakeholder set is larger — and rarely aligned
Founders, CEO, board members, and often investors all weigh in on a revenue leadership hire, frequently with different definitions of the ideal candidate. One wants an operator, one wants a closer, one wants someone who has taken a company through the next stage of scale. If that is not resolved before sourcing, the search restarts after the third candidate — not because the candidates were weak, but because nobody agreed what they were being measured against.
Compensation is structured differently
At leadership level, the mix shifts toward base, equity enters the conversation, and the negotiation stops being purely about cash. Candidates ask about scope, org design, hiring budget, headcount they can add, how the number was set, and who owns the parts of the funnel they do not control. A negotiation run as though it were a rep offer tends to lose the candidates you most wanted.
The cost of a wrong hire compounds
A bad account executive costs you a territory for a couple of quarters. A bad VP of Sales costs you the hiring plan, the reps they hired under it, the process they installed, and typically two to three quarters of momentum before anyone is willing to say it is not working. The damage is not linear with seniority, which is why leadership search justifies a slower, more evidence-driven process than any individual contributor hire.
For a longer walk-through of the search itself, read our guide to hiring top-tier sales leaders.
Sales leadership roles we place
Every level of the leadership ladder owns a different job. We scope the search to the layer you actually need, not the title that sounds most senior.
Sales Managers (First-Line)
The closest leader to the floor. They own ride-alongs, deal coaching, pipeline reviews, and the day-to-day performance of six to ten reps. At this level the hire lives or dies on coaching ability and willingness to stay in the details — a manager who only inspects dashboards does not move a team.
Directors of Sales
Usually the first layer that manages managers, or a large single team across territories. Directors own segment or regional performance, hiring and ramping their own reps, and translating a VP's plan into weekly execution. They are also where most future VPs are identified.
VPs of Sales
Own the number, the forecast, the team structure, and the plan to hit it. Depending on the company, they also own comp design, enablement, sales ops, and part of the go-to-market strategy. This is the role where scope definition matters most, and where VP of Sales recruiters earn their value by getting it defined before sourcing.
Chief Revenue Officers
Accountable for the whole revenue engine, commonly spanning sales, marketing, customer success, partnerships, and revenue operations. A CRO search is as much about org design and board reporting as it is about selling — the candidate has to run functions they have never personally carried a quota in.
Chief Sales Officers
Sales-focused executive ownership at the top of the org: field leadership, sales strategy, coverage models, and building the leadership bench beneath them. Often the right title when marketing and customer success sit elsewhere and the mandate is depth in sales rather than breadth across revenue.
Heads of Sales Development
Own the top of the funnel: SDR hiring and ramp, outbound methodology, message testing, meeting quality, and the handoff to closers. A frequently underweighted leadership hire — pipeline creation is where most revenue plans quietly fail, and this is the person accountable for it.
How we evaluate sales leaders
This is where a sales executive search is won or lost. Seven things we will not skip on a leadership assessment:
Evidence they built and retained a team
We establish what the team produced, not what the leader produced. How many reps did they hire, what share of the team attained quota, how long did their people stay, and did the team's performance hold after the leader moved on? A leader whose number was mostly their own deals is a different hire than one who built a bench that outlasted them.
Forecast accuracy and pipeline discipline
We ask what they called at the start of each quarter and what actually closed, and how they built the call. Leaders with real discipline describe their inspection cadence, stage definitions, and the deals they pulled out of the forecast early. Leaders without it describe optimism. Forecast credibility is what a board is actually buying.
Did they design the system or inherit it?
Playbook, sales process, territory model, comp plan — we determine, specifically, which of these the candidate built and which they were handed. Both histories are legitimate, but they predict very different performance depending on whether your role requires building from nothing or operating an existing machine well.
Hiring track record — and whether the hires produced
A leader's most leveraged skill is hiring. We look at how many reps and managers they hired, how they screened, how those hires ramped, and how many were still producing a year later. We also ask about the hires that failed and what they changed afterward. A leader who cannot name a hiring mistake has not looked closely enough.
How they handled underperformance
This is where leadership judgment shows. How fast did they identify a struggling rep, what did they actually do about it, how long did they let it run, and how did they handle the exit? Leaders who avoid the conversation carry underperformance for quarters; leaders who move too fast churn people who would have ramped. We probe both failure modes.
References from former direct reports, not just managers
Executives are well-practiced at managing upward, so a glowing reference from a former CEO is weaker evidence than most people assume. We take references from people who reported to the candidate: were they coached, was the forecast honest, did the leader defend the team, would they work for them again? This is often the most revealing part of the process.
Scope match against your actual org
We compare the candidate's real span of control — headcount, functions, revenue stage, deal size, motion — against the seat you are filling, and we name the gaps rather than paper over them. A leader stepping up two stages at once or down from a much larger org is sometimes exactly right, but it should be a decision you make knowingly.
We wrote more about the mechanics of this in what the best executive sales recruiters actually do.
Our executive search process
Four steps, run the same way on every leadership search — with alignment and confidentiality handled before a single candidate is approached.
Discovery & Stakeholder Alignment
Before sourcing, we get the founder, CEO, and board aligned on one definition of the hire: what the seat owns and explicitly does not own, the number and how it was set, the org beneath and beside it, comp architecture including equity, and the stage of leader this actually calls for. If the search is confidential, we agree here who knows, what can be disclosed, and which channels are off limits.
Market Approach & Vetting
We approach sales leaders who are performing where they are — the strongest ones are not in the market. Every candidate is screened on team output, forecast accuracy, hiring record, system ownership, and how they handled underperformance. On confidential searches, your company stays unnamed until a candidate is qualified and under confidentiality.
Shortlist
You receive a short, ranked slate — in as little as three days — with written assessments covering each candidate's team results versus personal results, stage fit, scope match, comp expectations, and the specific risks in hiring them. No résumé dumps, no volume padding, and no candidate presented without the reservations stated.
Close, References & Onboard
We run deep reference work including former direct reports, then stay engaged through a negotiation that covers scope, org design, hiring budget, and equity alongside cash. After the offer we help structure the first ninety days — what the leader is accountable for and when. Every placement is backed by our 60-day guarantee.
Why companies choose us for sales leadership search
Four things we hold ourselves to on every executive sales search.
Shortlists in as little as 3 days
Because we recruit sales leadership continuously, we are not starting from zero when you call.
Placement retention
We optimize for leaders who stay and build, not for filling the seat quickly.
Placement guarantee
Every placement carries a 60-day guarantee. We stand behind the hire, not just the introduction.
One function, done deeply
A Miami-based, sales-only search firm placing SDR through CRO. We do not recruit for every department.
Leadership search is one part of what we do — you can review the full range of recruiting services we offer employers, or talk to us about a leadership seat you need to fill.
Executive sales recruiting FAQ
Hiring a sales leader?
Tell us what the seat owns, what the number is, and whether the search needs to stay confidential. We'll come back with a vetted leadership shortlist in as little as three days, backed by our 60-day placement guarantee.