Head of Sales

tl;dr

• Agave is profitable, cash-flow positive, and fresh off a $15M Series A led by Accel ($20M+ total funding). You'll work directly with our CEO/co-founder to build and lead our sales team, taking Agave from $Xm to $XXm ARR+.

• You'll start hands-on. You'll initially carry a book alongside our AEs, because the fastest way to learn this motion is to do it. After, you help build and scale the machine: recruiting and ramping reps, coaching the team, owning forecast and pipeline, and standing up less-mature motions like outbound and cross-sells. From that point on, your number is the team's number.

• We're looking for 5+ years closing B2B SaaS deals, 2+ years managing quota-carrying AEs, and experience at a startup at or near our stage. Construction experience is a plus, not a requirement. In-person in SF strongly preferred. Learn more about us here (link).

Why are we hiring this role?

• We've hit product-market fit on our core product: 5XX+ customers, $Xm ARR, profitable and cash-flow positive for 2+ years. The core motion works and converts. What we don't have is someone who can scale it past our current stage.

• Our CEO/co-founder has been the acting head of sales since day one and is now the bottleneck on coaching, hiring, defining and training new sales motions, and many more critical tasks. This role takes that over.

• You'll step into a motion that already works: refined collateral, meeting templates, a clean CRM, SEs who run demos and handle domain depth, and strong inbound and referral volume converting at a high rate.

• Most sales managers just inherit a machine and keep it running. You'll grow the current system and help build what doesn't yet exist, like defining pricing and value props for new products on our growing platform, hiring and retaining talent for new roles, and much more.

• No CRO planned above this role; you own the function and report to the co-founder/CEO

Responsibilities

Your first 1-2 quarters: learn the motion by running it; earn the team's credibility by out-working them.

• Carry a personal quota. You'll join our AE rotation and run your own discovery calls, demos (with our Solutions Engineers), proposals, and negotiations. You’ll learn to repeat our current system well before doing anything else.

• Audit everything. You’ll sit in on rep calls, review and improve our CRM, talk to tons of customers and partners, and come back with a written view of what's working, what's broken, and what you'd change and why.

After that: grow the team and the machine

• Recruit and ramp. The highest-leverage thing you'll do. Source, interview, hire, and onboard our next AEs and other GTM roles. Own the ramp plan and the ramp timeline.

• Coach and develop. 1:1s, call reviews, and deal coaching that make each rep measurably better. Diagnose where deals stall and unblock them. Manage underperformance directly and early.

• Own the team’s output. You'll carry the team's aggregate quota and be accountable for every rep hitting their individual one. Own pipeline health, forecast accuracy, and CRM hygiene. Know exactly where the number is coming from, and where it’s headed and why.

• Turn what works into a playbook. Call scripts, templates, CRM workflows, dashboards, enablement, territory and quota design proposals. Run a weekly Sales Review with the whole company.

• Partner with the founders. ICP definition and GTM strategy for each product launch, pricing and packaging structure for existing and new products, and the GTM hiring plan. You'll work with Account Management, Partnerships, Delivery, Product, and Engineering on anything that touches our customers.

What this role is not

• Not a pure management seat. You'll carry a personal quota initially, since the best way to learn is doing. If you haven't personally sold in a while, this will be uncomfortable. You need to earn the team’s trust and respect early. After ramping, you’ll stop carrying an individual quota and lead the team.

• Not Partnerships or RevOps. We have people who own our partner motion and revenue operations. You own the direct sales team.

• Not a large org on day one. You'll work with 4 AEs, hire more by year-end, and grow the team and its scope from there. Scope grows with results.

Requirements

Hard requirements

• 5+ years closing. You've carried a quota at a B2B SaaS company and consistently exceeded it. You know what it takes to run a competitive deal and win it.

• 2+ years managing AEs. You've directly managed quota-carrying reps and hit a team number, not just your own. You've hired, ramped, coached, and let people go, and you can walk us through a specific example of each.

• Startup stage fit. You've done this role (or similar) at a company at or near our size and grown it from there. Someone whose experience is running a team inside a large, established sales org may struggle here, because most of the job is building things that don't exist yet without the abundant resources of a larger company.

• Motion fit. You've sold five-figure deals with fast sales cycles and inbound-skewed lead flow. Our motion is high-throughput, not six-month enterprise cycles.

Must have

• strong tenure (3+ yrs) at 1+ company (ideally multiple)

• upward trajectory (multiple promotions) at 1+ company

• experience as sales leader or top sales IC at high-growth startup

• based in SF, or willing to travel to SF HQ at last 1 week per month

Nice to have

• construction tech or a similar blue-collar vertical is strongly preferred; we'll make exceptions for strong fit on other dimensions

• Familiarity with accounting or ERP concepts

• You bring 1-2 strong reps with you (sign of the best candidates)

• Has worked in a senior/leadership sales role (VP, Director, Head of Sales) for 1+ years

• Has directly contributed to $X-XXm ARR revenue growth to a scaling startup in <1-2 years

• Worked through multiple stages of company growth (e.g. Series A —> Series C)

• Multi-product platform sales experience

• Experience co-selling with channel partners; you and your team will regularly co-sell with partner partners across the construction tech ecosystem

What we're looking for

• Proactive builder. Self-directed, fills gaps without being asked. We can trust you to disqualify a poor-fit customer instead of signing them, and to hold your team to the same bar.

• Coaching ability. You can watch a call, name the one change that would have moved the deal, and teach it in a way that sticks with motivated reps.

• Clear, persuasive communication. You write crisp emails and document, and can generate sharp counterpoints to customer hesitations on the fly. You raise your team's communication abilities.

• Reads people well. You know when to listen and when to push, and when a rep needs pressure versus backing.

• Product curiosity. You want to understand how the product actually works, in more detail than is typical for a salesperson.

 

Location

• In-person in SF strongly preferred. Our team has been fully in-person since day one, and this role is coaching-heavy, which works better in a room.

• We'll consider exceptional remote candidates in the US

Interview Plan

1. Intro Screen (30 min.) [Virtual] informal chat for you to learn more about the role. We'll ask for details on your past roles and what you're looking for next. We want to know that you meet our basic requirements and can speak about your work clearly. You’re welcome to ask lots of questions about whether working at Agave makes sense for you.

2. Experience Deep Dive (1 hr) [Virtual] deeper dive into your sales experience with our CPO. We'll ask for details on your sales history and dig into 1-2 of your most challenging deals/sales projects to learn more about your background. You’ll have 5-10min at the end to ask us any questions you’d like

3. Mock Sales Call (1 hr) [Virtual] mock sales call where an Agave co-founder plays a prospect, and you run a discovery call and drive next steps. We provide detailed directions in a Google doc and you spend ~3 hours preparing for the call.

4. Sales Coaching Session: [Virtual] Role-play where you will provide coaching on previous calls to Account Executives.

5. Onsite (60 min. x 5 people) [In-person in SF; we pay for your trip]: you'll interview with each co-founder and other members of our team. This will be a deeper dive into your experience, sales fluency, and overall fit. Each interview is 1hr: 45min for our questions and 15min for yours.

6. Call with our main partner at Accel. (45 min.) [Virtual] Our main partner at Accel will discuss the role and responsibilities in depth.

7. Reference Checks: References from 2-3 former reps and 1-2 former managers.