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Sean SheeheSS
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Sean Sheehe

@seansheehe

Customer onboarding director at Toast who nearly doubled segment productivity and raised First-Time-Right quality by 18 points.

United States
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At Toast, I built and scaled onboarding organizations across SMB, Mid-Market, Regional Mid-Market, and Multi-Unit. I led a multi-year operating transformation that nearly doubled segment productivity by improving capacity planning, performance standards, enablement, and customer-health visibility.

Most recently, as Senior Onboarding Manager, SMB, I led eight consultants across a rolling portfolio of approximately 1,500 implementations. We delivered 2,100+ go-lives from January to July 2026 at 130% of quota, and First-Time-Right performance rose from 58% to 76% in five months.

As Director, Upmarket and Multi-Unit Onboarding, I directed a 27-person organization across Mid-Market, Regional Mid-Market, and Multi-Unit. I developed a specialized administrative-support model that increased productivity 36% and returned 4.2 hours per consultant per business day to customer-facing work.

Earlier, I managed regional field implementations and restaurant operations, including delivery operations for ORDERUP, A GROUPON COMPANY. My approach moves from micro to macro: develop the person, improve the customer moment, then build the system that makes better performance repeatable.

Experience

Work history, roles, and key accomplishments

Toast, Inc. logoTI

Senior Onboarding Manager, SMB

Aug 2024 - Aug 2026 (2 years)

Led eight onboarding consultants across a rolling portfolio of approximately 1,500 active restaurant implementations, with responsibility for activation performance, implementation quality, capacity, and backlog health. Delivered 2,100+ go-lives from Jan to Jul 2026 at 130% of quota, exceeding target in all seven months and averaging 300+ activations per month.

OC

Delivery Operations Manager, Greater Baltimore

OrderUp, a Groupon Company

Nov 2016 - Oct 2017 (11 months)

Promoted from the Towson market to Greater Baltimore operations, leading two direct reports and 300+ independent contractors across 500+ restaurant partners. Operated the network's most profitable market at $3.75 gross profit per delivery while supporting 20,000 weekly deliveries.

SL

Financial Operations Coordinator

SmartLink, LLC

Sep 2015 - Nov 2016 (1 year 2 months)

Coordinated budgets, milestones, documentation, and time-and-expense billing for wireless infrastructure programs serving major US carriers; maintained job-cost and project databases.

Education

Degrees, certifications, and relevant coursework

Tuck School of Business at Dartmouth logoTD

Tuck School of Business at Dartmouth

Executive Education, Communicating Strategy

2024 - 2024

Completed executive education in Communicating Strategy.

Harvard Business School Online logoHO

Harvard Business School Online

Executive Education, Organizational Leadership

2024 - 2024

Completed executive education in Organizational Leadership.

Cornell University logoCU

Cornell University

Executive Education, Executive Presence

2023 - 2023

Completed executive education in Executive Presence.

Tuck School of Business at Dartmouth logoTD

Tuck School of Business at Dartmouth

Executive Education, Communication for Organizational Alignment

2023 - 2023

Completed executive education in Communication for Organizational Alignment.

Towson University logoTU

Towson University

Bachelor of Science, Geography and Environmental Planning

Activities and societies: NCAA Division I Men's Lacrosse; Dean's List; Head Coach, Rock Lacrosse (2016-2018); Assistant Coach, Hempfield HS Lacrosse (2012-2014)

Bachelor of Science in Geography and Environmental Planning with a minor in Business Communications.

Tech stack

Software and tools used professionally

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