Head of Sales

About Modern Modern is an AI-native data and intelligence platform for commerce brands, and an ai Residency that runs on it every day. That second part matters more than it sounds. Most analytics and AI tools for e-commerce are built by people who have never had to defend a media plan to a founder on a Monday morning. Ours isn't. Modern's ai Residency team operates a portfolio of DTC brands using this exact platform. Attribution, cohort analysis, media mix, creator performance, lifecycle, and every feature we ship has already survived contact with real P&Ls and real clients. So when we say the product works, we're not pointing at a demo environment. We're pointing at the brands we're accountable for. We're now taking the platform to market on its own. This is the first sales hire for that effort. The Role You are the first dedicated seller at Modern. Not the first sales leader managing an existing team, the first person whose job is to figure out how this product gets sold, then prove it by selling it. You're walking into real momentum. Warm inbound, a customer base that already loves the product, and a team that generates a steady stream of qualified conversations. What you'll build on top of it is the repeatable playbook: who buys, why, how fast, at what price, and through which channel. That comes together fast or it doesn't count. This category is being defined right now and the AI landscape resets every few months, so the bar is a working motion inside your first quarter and proof it repeats in the quarter after. You'll build it the only way it can be built, by selling. This is a player role first. You carry the number, run the deals, and write the playbook out of your own wins. A team comes later, hired alongside growth rather than ahead of it, and you'll lead reps running a motion you proved yourself. If you want to manage a team on day one, this isn't it. If you want to own a go-to-market from zero, keep reading. What You'll Own Pipeline generation and strategy. You decide where the next hundred customers come from. Outbound, partnerships, communities, events, the Modern's network, affiliate and referral channels. You test, measure, and double down on what works. Selling across four motions. Modern reaches the market in more than one way, and you'll need to build for all of them: - Self-serve / product-led: converting and expanding signups who found us on their own - Mid-market brands: demo-led sales cycles with $5M–$50M+ commerce operators - Enterprise and strategic accounts: longer cycles, multiple stakeholders, custom scope - Agencies and partners: selling Modern as infrastructure other operators build on These behave very differently. Part of the job is figuring out where to concentrate first rather than doing all four badly at once. Expert-level product fluency. You'll be trained on the full platform and expected to know its entirety. Not the pitch, the product. You should be able to run an unscripted demo against a prospect's real data, answer a technical objection without a solutions engineer in the room. Pricing and packaging feedback. You'll be the closest person to how buyers actually react to our pricing. That signal comes back to leadership and shapes what we charge. Product feedback loop. Every lost deal has a reason. You'll bring those reasons to the product team with enough specificity that they're actionable. Building the team. Once the motion is proven, you'll hire and lead the reps who scale it, and you'll have built the playbook they run. What Success Looks Like First 30 days: You know the platform as well as anyone at the company. You've sat in on ai Residency client calls to understand how brands actually use it. You've talked to at least 15 existing customers about why they bought and what nearly stopped them. First 90 days: You've defined the ICP with evidence, not intuition. There's a documented sales process, a working demo narrative, and a pipeline you built. First closed deals sourced by you. First 6 months: A repeatable motion with predictable conversion rates. You can tell us what it costs to acquire a customer and how long it takes. First 12 months: Consistent quota attainment, a case for which motion to scale, and a hiring plan you're ready to execute. Who You Are You've done 5+ years of B2B SaaS sales, with a track record you can speak to specifically. Numbers, deal sizes, cycle lengths, how you sourced your pipeline. We'd rather hear about one hard deal you won than a list of logos. You're genuinely technical. Not "comfortable with technology," actually technical. You can talk about APIs, data integrations, and attribution methodology without deflecting to an engineer. You've probably built something yourself, even if it was scrappy. You live in the AI landscape. You're following what's shipping, you have opinions about where it's going, and you can explain to a non-technical brand owner why any of it matters to their business. This industry re-prices itself every few months; you need to be someone who enjoys that rather than someone who tolerates it. You've sold in ambiguity. Early-stage, no playbook, figuring out the ICP while carrying a number. You know the difference between that and selling an established product with a full marketing engine behind you. You understand commerce. You know what CAC, MER, LTV, and contribution margin mean to an operator, and why a brand's answer to "is this working?" is harder than it looks. Direct DTC or e-commerce experience is a strong plus. You're a builder, not a maintainer. You'd rather write the first version of something than optimize the fifth. Bonus Points - You've been an early or first sales hire before and can describe what you'd do differently - Experience selling both self-serve/PLG and enterprise motions at the same company - You've sold into agencies, or worked at one - Background in martech, analytics, attribution, or commerce infrastructure - You've used AI tooling to build your own prospecting or research workflows Why This Role A product that already has proof. You won't be selling a roadmap. A portfolio of brands runs on this platform daily, and the results are documented. Real ownership. You're defining the go-to-market, not executing someone else's. Your decisions become the company's sales strategy. Direct access. You'll work with leadership daily. No layers between you and the decisions. Honest about the stage: this is early. Some months will be messy. The systems you want will often be the systems you have to build. We think that's the appeal, but it should be an informed choice. Benefits Competitive salary Competitive health benefits Unlimited PTO Health and wellness credit Fully remote A front-row seat at an AI-native company building the future of how brands and creators work together