Toast, Inc.Heading into 2024, I faced a territory quota nearly 30% higher than the prior year, compounded by Toast's push into new hospitality verticals I hadn't previously sold into. Rather than treat this as a headwind, I saw it as an opportunity to build a more disciplined, data-driven sales motion from the ground up.
I built a targeted outbound strategy centered on a top-25 whale account list, partnering closely with XDRs to map buying committees within each target organization. I also leveraged AI GTM tooling I helped beta-test to prioritize high-propensity accounts, combining this with rigorous Salesforce hygiene and pipeline management to run more concurrent high-ARR opportunities than my peers. This approach let me systematically break into unfamiliar hospitality segments while maintaining deal velocity across a larger, more complex pipeline.
The results were significant both individually and organizationally: I closed $2.2M in ACV, booked $1.7M in ARR, and brought $1.1M in ARR to live revenue. Finishing the year at 202% of quota and ranked #2 out of more than 650 reps company-wide. Beyond my own numbers, I partnered with Toast's product, AI, Data Science, and GTM teams to help conceptualize and beta-test the company's first internal AI GTM tooling, which was ultimately scaled across the entire sales organization. I also documented and shared my whale-account outbound methodology, helping other AEs adopt a more targeted approach to enterprise prospecting. This ultimately saved each AE hours of admin time per week across the field organization.
