Founding Account Executive

Founding Account Executive

Diagonal is building the future of personalized software. Our core team has deep experience in vertical SaaS and crafting systems at scale. We're backed by leading investors and are setting the foundation for a platform that redefines how software adapts to its users.

We're looking for a Founding Account Executive to help build the foundation of our go-to-market motion. This is a true early-stage sales role. You won't be handed a mature pipeline or a polished playbook — you'll help create them. We're looking for someone who enjoys the full sales process: sourcing prospects, cold calling, outbound outreach, running demos, and closing deals.

You'll work directly with the founders to shape how Diagonal grows. That means refining messaging, identifying ideal customer profiles, experimenting with outbound strategies, and helping turn early traction into a scalable sales engine.

Our customers are SMB businesses looking for software that adapts to how they operate instead of forcing them into rigid workflows. Your job is to help them understand what's possible and guide them through that transformation.

If you thrive in fast-moving environments, enjoy building momentum from scratch, and love the process of winning customers, you'll thrive here.

Responsibilities include owning the SMB sales cycle from outbound prospecting through close, sourcing and qualifying new opportunities through cold calling, email outreach, LinkedIn, referrals, and creative outbound strategies, running discovery calls and product demos tailored to each customer's workflows and pain points, building and managing your own pipeline while maintaining strong CRM hygiene, working directly with founders to refine messaging, positioning, and outbound strategy, gathering customer feedback and helping shape both product direction and go-to-market strategy, experimenting with outbound tactics, messaging, and sales processes to improve conversion rates, and developing a deep understanding of Diagonal's platform and communicating its value clearly to business owners and operators.

This role is for someone who wants to help build the sales engine from the ground up — not just plug into an existing machine. Success in this role means not only closing new business, but helping us define a repeatable SMB sales motion. In your first 6–12 months, you'll be expected to generate qualified pipeline, close early customers, surface repeatable messaging and objections, and help turn founder-led selling into a scalable process.

You'll have significant ownership, direct access to the founders, and the opportunity to shape how Diagonal grows. We're looking for someone hungry, resourceful, and excited to create momentum every day.