Head of Sales

TL;DR - Agave builds applied AI for construction, fresh off a $15M Series A from Accel and YC ($20M+ funding to date). Our AI agents run on proprietary rails into the systems contractors already use, and AI is the fastest-growing part of the business. You'll build and lead the sales org that takes Agave from $X-XXm to $XX-XXXm ARR over the next 3 years, reporting directly to our CEO/co-founder. - Your success will be the team's output. You’ll recruit and ramp new sales reps, coach the team, own forecasts and pipeline, build less-mature sales motions, help close strategic deals, and develop sales leaders under you. - We're looking for someone who has built and led a strong sales team at a fast-growing startup at/near our stage with an overlapping GTM motion to ours. Construction/blue-collar vertical sales experience is preferred, not required. In-person in SF strongly preferred, and willingness to travel here often if you’re remote is required. Learn more about us here (link https://www.figma.com/slides/nlpdpvRj3iS2qbPXqkMQz0/Agave--Candidate-Pitch-Deck?node-id=5-610&t=jDDiUrnFNhn2TWMm-1). WHY ARE WE HIRING THIS ROLE? - We've hit product-market fit on our core product: 600+ customers and $X-XXm ARR. The core motion works and converts predictably. Our AI products are the fastest-growing part of the business: a third of new deals now include one, and we signed 8 new channel partnerships in the last month alone. What we don't have is someone who can scale it past our current stage, as we expand our platform to many products with individually significant revenue streams. - 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 and expands it going forward. - 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. - 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 expanding platform, hiring and retaining talent for new roles, building new motions from scratch. - No CRO planned above this role; you own the function and report to the co-founder/CEO. As the team grows, you'll lead a growing sales org and manage sales managers by end of 2027. WHY THIS IS A CAN'T-MISS ROLE - The market is enormous and under-built. Construction is a $12T global industry running on software built 20-50 years ago, much of it on-prem with no APIs. We spent 3 years building the rails to read and write across those systems, and we use them to deploy AI agents for invoicing, expenses, compliance, billing, financial reporting, risk-tracking and more. - AI products customers already buy. If you're at a SaaS company bolting AI onto a legacy product, or at an AI-native company still looking for product-market fit, this is the third path: AI agents built on rails no one else has, sold into hundreds of customers through a motion that already converts. - You'll scale the sales org of a generational company. The next 3 years take Agave from $X-XXm to $XX-XXXm ARR, and the org that carries it is yours to design: the reps, the managers under you, the motions, the playbooks. - Early-stage upside without early-stage risk. 600+ customers, hockey-stick growth, and a $15M Series A from Accel. You get the ownership and scope of a Series A with a downside most Series As don't have. - Backed by people who've done this in construction. Accel, YC, and investors and operators from Procore, Autodesk, PlanGrid, and Plaid. - Direct line to the CEO, no CRO above you, and a mandate to build leaders beneath you. This is the seat where you do the best work of your career, and the title and scope grow with it. RESPONSIBILITIES From day one, the team's number is yours. - Own the team's output, across new-logo and expansion revenue. 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. - Roll-up your sleeves and help close strategic deals alongside your team. You’ll build fluency in the nuances of our motion during onboarding so you can help AEs close large, strategic deals that materially impact our top-line revenue. - Audit everything and improve the system. 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. 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. - 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. - Build new motions. Grow our outbound motion and SDR team, and mature our expansion/cross-sell motion to drive growth. - Take AI products to market. Pricing, packaging, and the sales motion for each new AI product, including larger expansions into our biggest accounts. - 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. REQUIREMENTS Required - Hands-on selling experience. You've personally closed deals in the last few years, and you'll close deals here during your ramp to learn the motion. - Strong people management experience. You've directly managed reps and hit a team number. 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 faster sales cycles and inbound-skewed lead flow. Our motion is high-throughput, not six-month enterprise cycles. - In-person / willing to travel. Based in SF (preferred), or willing to travel to our SF HQ at least 1 week per month (minimum requirement). Strongly preferred - Experience selling in a construction/blue-collar vertical; we'll make exceptions for strong fit on other dimensions. - A track record of staying and growing: multiple promotions at 1+ company, no pattern of short stints. - Joined a company at an early stage (<$15m ARR) and helped take it to mid/growth/late stage. - AI fluency: you use AI daily in your own selling and management workflow, and you'd raise the team's bar for using it - Experience as a sales leader, or a top sales IC working under a great sales leader, at high-growth startup Nice to have - Several years closing B2B SaaS deals - You bring strong reps with you (sign of the best candidates) - Experience managing managers, or evidence you're ready to - Built or scaled an outbound or SDR function - Multi-product platform sales experience - Experience co-selling with channel partners; you and your team will regularly co-sell with partner reps 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 documents, 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. BENEFITS Compensation - Equity: competitive equity, so you share in the upside you’re helping create. - Performance Bonuses: we offer annual performance bonuses when we hit company growth goals. For 2026, the bonus is 15% of your base salary or OTE. We've had these bonuses for the last 3 years, and expect to continue to have them in subsequent years. - 401(k): we match 100% of your contributions, up to 4% of your annual salary. Health & family - Healthcare: we cover 90% of your healthcare costs, with several plan options. We also cover a healthy portion of dependent costs. - HSA: a $100/month company contribution to your HSA. - Parental leave: up to 12 weeks of paid leave for all new parents, including adoptive and foster parents Where you work - Relocation: a sizable bonus if you’re moving to the Bay Area, plus an extra bonus for anyone (even current Bay Area residents) who moves within a 15-minute walk of our office. - Commuter benefits: pre-tax contributions toward commuting costs, and we cover the full cost of a Muni pass if you take public transit. - Office visits: company-sponsored trips to our SF HQ at least every other month. For remote teammates, we schedule trips to overlap during “remote visit” weeks so you get real time with the team. - Visa sponsorship: we sponsor visas (H1B, TN, etc.) for candidates who are a good fit. Perks - Food: breakfast and dinner stipends through DoorDash, plus a kitchen stocked with coffee, snacks, and drinks. - Gym: on-site gym with Peloton, squat rack, Tempo, Yoga setup, and more.