We're building Skyway, a platform to help companies find, procure, manage, and forecast hyperscaler, inference, and GPU infrastructure. With the explosive growth of AI, companies are signing the largest infrastructure agreements in history and doing it all with spreadsheets and fingers-in-the-wind. Skyway provides structure and data to make the problem suck a whole lot less. Our customers are the strategic finance and engineering leaders at AI labs, inference providers, neoclouds, and AI-native software companies who are making seven, eight, nine, ten-figure compute decisions using data that flows through our systems. Under the hood, we're turning unstructured agreements—hyperscaler private pricing agreements, AI lab MSAs and prepaid credits, neocloud reserved capacity—into structured data, dynamically recalculating bills against both contract and public pricing, and giving finance and engineering a single shared set of numbers for what they've consumed, are consuming, and will consume. Our goal is to be the system every AI-native company runs its compute strategy on: forecasting, scenario modeling, commitment tracking, invoice validation, benchmarking, and purchasing, all on top of the best proprietary pricing dataset in the world. Duckbill has spent the last seven years helping companies understand, manage, and negotiate their cloud and AI spend. We’ve worked with hundreds of enterprises, negotiated tens-of-billions in cloud and AI contracts, and built one of the best-known brands in the cloud world. What we haven’t had is a full sales team. Like a lot of startups, our founding AE has moved into a Head of Sales role after spending years closing deals with help from our Cloud Economists, negotiators, and product team. Now we’re scaling the team up. You’ll inherit demand, active opportunities, a known brand, and a market we’ve been working for years. You’ll also be expected to create pipeline, run deals, and help build a sales org that can scale. WHY THIS ROLE EXISTS Enterprise cloud and AI spend is changing faster than most companies can manage it. For years, cloud cost management mostly meant finding waste in an cloud bill. While that still matters, it is not enough anymore. Companies are now making large commitments across AWS, Anthropic, OpenAI, Azure, GCP, neoclouds, and inference providers without benchmarks, tooling, or visibility into whether the contracts they are signing are any good. In response, we’re building Skyway, our platform for managing commercial terms and compute commitments across cloud and AI providers. It comes directly from the work we’re already doing with customers: helping them understand their commitments, negotiate better contracts, and make better, more informed decisions for their business. The loop is simple. We help a customer with an expensive contract problem. That gives us trust and context. Skyway helps the customer forecast and manage those commitments over time. The next contract cycle gives us another reason to be in the room. That’s the business we need you to help build. WHAT MAKES THIS HARD The buyer is changing. While we still sell to FinOps and cloud cost teams at traditional enterprises, the best conversations are increasingly happening with AI-native or AI-active companies where engineering, finance, and infrastructure leaders are all circling the same problem. The first person to feel the pain might be in engineering, strategic finance, infrastructure, or procurement, and budget ownership may not be clear when you arrive. You have to be comfortable entering through whichever door is open and helping the company figure out who needs to be in the room. Sales cycles are usually 90 to 120 days. You’ll need to stay close to the account, keep the next step alive, and know the difference between real urgency and wishful thinking. We do not have an SDR team filling your calendar. Inbound is consistent and it converts well, but it will not carry the number by itself, so you’ll need to work to build pipeline on your own. WHAT YOU’LL DO Own the full sales cycle. Qualify, run discovery, manage follow-up, work the buying group, and close. Build pipeline continuously. Inbound opportunities, outbound, closed-lost re-engagement, referrals, events, partner conversations, and the Duckbill customer network will all be part of how you build your book. Take over real opportunities quickly. In the first 30 days, you’ll learn the market, the customer problems, the Duckbill story, and the way we qualify deals. After that, you should be running more of the pipeline with less hand-holding and taking over opportunities already in flight. Keep HubSpot useful. We know most salespeople would rather be selling than updating the CRM. Same. But if we’re going to build a truly extraordinary company and team, the CRM data has to be usable. Notes, next steps, closed-lost reasons, and deal context need to be current enough that all of us can learn from them. Run useful discovery. We work closely with the product team, so we’ll want you to tell us what you are hearing: where buyers are confused, where the pitch is landing, and where the offer needs to change. We need you to notice those patterns. HOW WE WORK You’ll get more ownership than you may be used to. We are a small team, around a twenty people today, and we hire people who can take responsibility without needing every step prescribed. We care about pace and follow-through. If you say you are going to follow up, follow up. If a deal is not real, say so. If HubSpot is wrong, fix it. We use AI throughout the company and expect you to as well: account research, call prep, follow-up, summarization, messaging tests, pipeline analysis, and whatever else helps you do better work faster. AI skeptics will not do well here. ABOUT YOU You probably came up through SDR. You know how to create pipeline because you have done the work yourself, not because leads showed up neatly assigned in a queue. You’ve been in an AE role for 2 to 3 years and are ready to own a book that is actually yours. You can run volume without letting the details fall apart: 30-plus active opportunities, multiple people involved in each deal, and a pipeline that constantly needs to be refilled. You do not need to be a cloud or AI expert on day one. You do need to be curious. If a conversation turns technical, you should lean in, not check out. You are not scared by a big number. We expect you to sell, not sit back and sort inbound, and we pay accordingly for those results. We do not expect you to arrive fully ramped on day one, but we do expect you to be excited by the size of the opportunity and willing to do the work required to earn it. We strongly prefer someone in San Francisco. Our market is concentrated here, and events, dinners, and face time with customers are part of the job. THIS ROLE IS NOT FOR YOU IF… You need a large support org around you. You’ll have support from our Head of Sales, founders,, a strong technical team, and a real product to sell. You won’t have a team of BDRs, SEs, and proposal writers doing the surrounding work. You want a whale-hunting role where you spend most of the quarter on two or three accounts. There will be big deals here, but this job is higher-volume than that. You need to be able to keep 30-plus real opportunities moving without losing the thread. Your plan is to work inbound and “get to outbound later.” Inbound matters here, but it will not carry the number. You need a fully formed category before you can sell. Buyers will not always have a clean budget owner, buying process, or internal vocabulary for the problem. You roll your eyes at AI as a daily productivity tool. We use it everywhere, and we expect the same from the sales team. OUR UNFAIR ADVANTAGES We've been doing customer research for seven years. Duckbill started life as small boutique services firm in 2019 working primarily with large enterprises. Through that work, we've had a front row seat to the hardest problems organizations face. As a result, our vision for Skyway isn't built on hypotheses: it's built on having directly worked these problems alongside the people who live with them every day. Services are our superpower. Customers seek us out for our contract negotiation expertise, process, and proprietary benchmark data, a motion that started with AWS and expanded to Azure, GCP, and now to inference and neocloud providers. Every negotiation engagement teaches us something new about customer pains which feeds right back into the product, creating an great feedback loop between services and product. (And don’t worry, our engineering team is separate from our services team, so no FDE here.) Everyone knows us. We operate the largest AWS community outside of AWS itself—35,000 newsletter subscribers, 5 million podcast downloads, 100,000+ social media followers. That reach, plus the relationships we have inside the hyperscalers, AI labs, and neoclouds, means we aren’t building a sales pipeline from scratch. ABOUT DUCKBILL We are a small and growing team of ~15, which means you get the opportunity to be on the ground floor of building the product and company. Our founders are domain experts in the market+problem space, bringing deep industry and customer connections in cloud and compute economics to the product. We're backed by Heavybit and Uncork Capital, having raised $7.75 million, along with substantial revenue.