‍About Owlery

Owlery is the AI platform replacing the spreadsheets and rigid legacy software that mid-market shippers still rely on to manage logistics. Brands and manufacturers you know and love rely on Owlery to cut freight costs 5-15%, automate 10-20 hours per week of manual workflows, and get real time visibility across their supply chain. We’re a small team building a fast growing business (3.8x year over year) backed by institutional investors, and founded by Uber Freight veterans. 

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The Opportunity

Join as our first sales hire at a fast-growing logistics tech startup, reporting directly to the founder. You'll build our sales motion from the ground up and have direct influence on product, GTM strategy, and company direction. This is a chance to define how we scale and build the team you'll eventually lead.

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This is a pipeline-building role first and foremost, a true founding sales role. You'll own the full sales cycle, not just executing someone else's playbook but helping to write and shape it. Your job is to help define how we scale efficiently while building pipeline and closing deals.

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We are a remote-friendly company with offices in the San Francisco Bay Area. If you don't live here, we'll fly you out regularly with the rest of our remote team.

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This role is perfect for someone who:

• Knows freight and logistics inside-out and can speak the language of shippers from day one
• Gets energy from hunting - cold calling doesn't scare you, it excites you
• Is looking for equity and influence and is excited by having an outsized impact on the trajectory of the business
• Wants to leverage and sell AI into an industry that’s still doing things manually - and see the opportunity in that gap

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What you’ll do

• Build pipeline through outbound. Cold call, email, LinkedIn, events - whatever channel drives qualified opportunities. Bring fresh ideas for winning customers and we'll double down on what works.
• Own the full sales cycle. Take deals from first touch through close, partnering closely with our c-suite and founders on strategic accounts.
• Build the repeatable playbook. Experiment with messaging, segmentation, and outreach strategies. Document what works so you can scale it with future hires.
• Bring market signal back to the team. Your conversations with prospects will shape product priorities, positioning, and how we go to market.

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Who you are

• You have freight/logistics/supply chain experience. You’ve worked with shippers, you know their pain points, the players, and the industry dynamics. ‍
• 3-5+ years in B2B sales where you consistently hit or exceeded quota. 
• Full-cycle sales experience. You’ve done it all - outbound prospecting, running discovery calls, delivering demos, handling objections, closing deals. ‍
• Scrappy and self motivated. You don’t wait to be told what to do. You’re resourceful and figure out how to make things happen. ‍
• Excellent communicator. You write clearly and compellingly. You run engaging calls. You can break down pricing models, integration timelines, and ROI cases for non-technical buyers.‍
• You track your own pipeline metrics without being asked and use them to sharpen your approach.‍
• Experience with CRM and sales engagement tools (we use HubSpot, Apollo, and LinkedIn Sales Navigator, but we value selling ability far more than tool expertise).

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What you’ll get

• A real seat at the table. Your input will shape product, strategy, and how we go to market.
• Meaningful equity in the business. You’re joining early - your equity will reflect that in ISOs (options).
• Competitive comp. Base salary + commission with uncapped upside. Expected OTE of $170-300k+ depending on experience.
• Career growth. You're not just building pipeline, you’re building the playbooks, processes, and team that scale the company. 
• Premium benefits. Healthcare coverage including medical, dental, and vision plans, a company-sponsored 401K plan, and FSA.
• Unlimited PTO because we trust you to manage your time.
• Regular travel to meet face-to-face with the team and customers - we invest in getting remote teammates together often.
• Access to premium AI tools like ChatGPT Plus and Claude Pro to keep your workflow sharp.

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