Summary
Overview
Work History
Education
Skills
Accomplishments
Timeline
Generic

Ashley Voss

Chicago,IL

Summary

Senior Account Executive with 4+ years of B2B SaaS experience, consistently exceeding quotas with an average attainment of 140% over the past two years. Proven track record in selling to mid-market accounts, leading multi-stakeholder deals, and managing full sales cycles from prospecting through close. Recognized for strategic discovery, value- and ROI-driven selling, and close collaboration with customer success teams. Passionate about driving digital healthcare transformation and seamless integration.

Overview

4
4
years of professional experience

Work History

Senior Account Executive -SMB- Growth Business

Headway
NYC (Remote), New York
01.2024 - Current
  • Q3 '25 currently at 170% quota attainment
  • Q2 '25 at 147% quota attainment
  • Q1 '25 at 113% quota attainment
  • Achieved an average 140% quota attainment in 2024, driving over $1M in annual revenue.
  • Top performing AE with a 40% close rate vs. peers average of 20-30%.
  • Ranked 2/8 AE's in mid-market & enterprise sales team.
  • Closed largest deal in H1 2025 (SpringHealth Solutions $130,250 in TCV) by presenting a compelling business case on a claims lost saving initiative of at least 20% quarter-over-quarter.
  • Authentically manages customer relationships, generating 20% net-new business through referral solicitation and outbound prospecting.
  • Objection handle with value based selling across multiple C-suite stakeholders by quantifying ROI and clearly understanding pain points.
  • Leads weekly skill-development exercises to enhance peer sales efficiency and conversion rates, directly contributing to monthly team quota attainment.
  • Prioritizes time management to balance core role responsibilities with multiple cross-functional project DRIships, including delivering monthly and quarterly business reviews to Sales Leadership, driving product improvement initiatives based on client feedback with Product and Engineering teams, and supporting the Marketing lead on key initiatives tied to quarterly KRs.
  • Collaborated with Enablement, Revenue Operations, and Customer Success teams to successfully decrease customer onboarding time by 30% and improve product implementation by 40% in 2024.

Senior Account Executive- SMB- Small Business

Headway
NYC (Remote), NY
01.2022 - 12.2023
  • H1 '22 (ramping Q1 '22) at 107% quota attainment
  • H2 '22 at 108% quota attainment
  • Closed +340 net new and outbound small business deals in 2023, achieving Century Club (top 10%) and 114% in annual quota attainment.
  • Ranked 6/39 AE's in new outbound business generated in 2022 (89 referral leads generated)
  • Average close rate of 70% (peer average is 50%-60%) in 2023
  • Created and supported in the training and implementation of SME playbooks, improving value based selling for state specific markets and increasing average close rate by 10%.
  • Facilitated monthly presentations on objection handling, revenue operations, and competitor intel for ramping AE's.
  • Led as a Chair of Communication on our Small Business Culture Council, improving inclusivity and connection amongst remote AE's company culture and experience.

Account Manager

Angi
Chicago, USA
04.2021 - 12.2021
  • Averaged 102% quota attainment month-over-month.
  • Close role data/point
  • Managed a high volume of leads (40+ a month) and developed individual business cases that ensured my long term success.
  • Coordinated with clients and service providers to schedule work orders, and manage invoices.
  • Proactively created new business by referral solicitation, expanding Angi's service provider network by soliciting over 72 referrals, and my book of business by 20%.
  • Upsold existing business, resulting in $10K additional quarterly revenue.
  • Facilitated discussion groups with leadership, presenting on SMEs, sales strategies from top performers, and objective handling for the sales team's new and tenured account managers.

Education

Bachelor of Science - Community Health

Indiana University
Bloomington, IN
05.2016

Skills

  • Sales and Marketing
  • Closing Complex Deals
  • Cross-functional Collaboration
  • Lead Generation
  • Coachable
  • Team Player
  • Relationship Building and Management
  • Goal Oriented
  • Complex Problem Solving
  • B2B Sales
  • Healthcare SaaS Selling
  • C-Suite Closing
  • Enterprise Account Management
  • Strategic Prospecting & Cold Calling
  • Forecasting Accuracy
  • Salesforce
  • Outreach
  • Looker
  • Slack

Accomplishments

2024 ‘Act Like A Headway Owner’ Annual Sales Recipient - Awarded to one individual embodying all 9 company principles

2023 Headway ‘Century Club’ Annual Sales Recipient - Awarded to Top 10% of Highest Performing Sales Individuals

Timeline

Senior Account Executive -SMB- Growth Business

Headway
01.2024 - Current

Senior Account Executive- SMB- Small Business

Headway
01.2022 - 12.2023

Account Manager

Angi
04.2021 - 12.2021

Bachelor of Science - Community Health

Indiana University

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