Open to opportunities

Richard Goss

@richardgoss

Message

Director of Sales driving enterprise healthcare revenue through complex negotiations and team mentorship.

United States

Message

What I'm looking for

I’m looking to lead enterprise healthcare revenue growth, own forecasting and pipeline execution, and mentor AEs through complex multi-site negotiations—while partnering with executive leadership to drive predictable, above-quota results.

I’m a Director of Sales with 3+ years of success driving enterprise healthcare revenue at ShiftKey, consistently exceeding quota and delivering results you can measure. In 2025, I earned President’s Club and Salesperson of the Year after hitting 123% annual goal attainment.

During my time in enterprise and mid-market healthcare sales, I closed 230 accounts and delivered $30M in net new revenue. I lead regional enterprise sales strategy across multi-site healthcare systems, owning everything from pipeline management to revenue forecasting and territory planning.

I’m at my best in strategic account expansion—coordinating cross-functionally with Legal, Procurement, Finance, and executive leadership to navigate complex multi-location deal cycles. I also coach Account Executives on enterprise deal strategy, negotiations, and pipeline development, helping the team execute with clarity and confidence.

Experience

Work history, roles, and key accomplishments

Current

Director of Sales

Current

ShiftKey

Jan 2026 - Present (5 months)

Promoted to Director of Sales and led regional enterprise expansion across multi-site healthcare systems, generating $30M net new revenue and 123% quota attainment (2025). Coached Account Executives on enterprise deal strategy and negotiations while overseeing 210 active accounts, earning President’s Club and Salesperson of the Year (2025).

Enterprise Strategy Strategic Account Management Quota Attainment Pipeline Management Revenue Forecasting Cross functional Leadership Coaching

Senior Account Executive

ShiftKey

Jan 2022 - Jan 2026 (4 years)

Closed 230 enterprise and mid-market healthcare accounts, delivering $30M in net new revenue and 123% annual quota attainment (2025). Managed and expanded a 210-account portfolio and led complex multi-stakeholder sales cycles with legal, procurement, finance, and C-suite leaders.

Enterprise Sales Strategic Account Expansion Healthcare Sales Revenue Forecasting Stakeholder Management Salesforce Reporting

Motor Claims Consultant

CGU Insurance

Jan 2021 - Jan 2022 (1 year)

Managed a large motor claims caseload by prioritizing urgent matters and resolving complex claims using expertise in policy coverage and industry regulations. Negotiated favorable settlements and delivered tailored solutions for clients while maintaining a high success rate in claim resolution.

Motor Claims Policy Coverage Regulatory Compliance Claims Investigation

Hotel Manager

Somerset Hotel

Jan 2019 - Jan 2021 (2 years)

Managed hotel staff scheduling and daily operations, improving coverage during peak periods while increasing gaming revenue from Tier 2 (> $500K/week) to Tier 1 (> $700K/week). Led operations through COVID-19 and a change in ownership by implementing promotions, upgrading gaming machines, and strengthening social media to drive revenue.

Hotel operations management Staff Scheduling Gaming Machine Operations Change Leadership COVID 19 Operations Response

Education

Degrees, certifications, and relevant coursework

Midwestern State University

Bachelor of Science, Exercise Physiology; Biology

2017 -

Activities and societies: Student athlete; Deans List; Male Athletic Scholar of the Year (Midwestern State University).

Earned a Bachelor of Science in Exercise Physiology and Biology at Midwestern State University. Completed the program as a student athlete with Deans List recognition and Male Athletic Scholar of the Year honors.