Founding Account Executive

About Diagonal

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.
The Role

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

• Own the SMB sales cycle from outbound prospecting through close.
• Source and qualify new opportunities through cold calling, email outreach, LinkedIn, referrals, and creative outbound strategies.
• Run discovery calls and product demos tailored to each customer's workflows and pain points.
• Build and manage your own pipeline while maintaining strong CRM hygiene.
• Work directly with founders to refine messaging, positioning, and outbound strategy.
• Gather customer feedback and help shape both product direction and go-to-market strategy.
• Experiment with outbound tactics, messaging, and sales processes to improve conversion rates.
• Develop a deep understanding of Diagonal's platform and communicate its value clearly to business owners and operators.

A Final Note

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.

Requirements

• 2+ years of experience in SMB sales, outbound sales, or account executive roles at a SaaS company.
• Comfortable prospecting and cold calling consistently.
• Strong discovery and demo skills - able to guide conversations naturally and uncover customer pain points.
• Highly self-directed and organized in a remote environment.
• Excellent written and verbal communication skills.
• Competitive, driven, and excited by early-stage environments.
• Ability to move quickly, adapt fast, and wear multiple hats.
• Experience selling vertical SaaS, workflow software, or operational tools is a plus.
• Startup experience is a plus, especially at an early-stage company.

Benefits

• Competitive salary + commission + equity

• Fully remote team
• Discretionary PTO
• US Only: Top-tier Health Insurance (Medical, Vision, Dental)
• Top-of-the-line computers/equipment
• Paid parental leave