CHELSEA PEPPER
Pittsburgh,PA
Summary
Account executive with proven success in both Enterprise and Mid-Market SaaS roles. Proven success managing both rapid sales cycles and complex, technical, high-value transactions. Expertise in consultative selling and fostering cross-functional collaboration. Utilizing AI tools to engage C-suite executives, identify needs, and create customized solutions, resulting in record deal closures and consistent awards.
Overview
9
9
years of professional experience
Work History
SENIOR ENTERPRISE ACCOUNT EXECUTIVE
BlastPoint
Pittsburgh, PA
09.2025 - Current
- First Enterprise AE hire; developing a comprehensive playbook to establish sales processes and strategies using a combination of sales methodologies and AI.
- Engage with VPs and C-suite executives to identify business needs and present tailored solutions.
- Attend industry events and conferences to cultivate relationships and expand book of business.
- Create and execute messaging for outbound efforts, marketing initiatives, and tradeshow events.
- Work closely with engineering, product, Solutions Consultant, other AEs, as well as CEO, CTO, and VP of Sales on strategy and planning.
- Manage full sales cycle from multi-threaded outreach through deal close.
Senior Enterprise Account Executive
Gladly
04.2024 - 09.2025
- Closed the largest enterprise deal in 2024 of $1.5M TCV within the first 7 months with an average sales cycle of 12-36 months.
- Engaged with C-suite personas, including CTO, CRO, and CIO, to tailor solutions that addressed strategic business needs.
- Managed hybrid book of business with current customers and net new logos, resulting in significant upsell and cross-sell opportunities.
- Received Rookie of the Year award for 2024 and achieved the highest plan attainment of the Enterprise team at 98% of goal.
- Collaborated with SC, product, and engineering teams to navigate complex sales cycles, ensuring alignment and effective solution delivery.
- Worked with companies with $500M+ in yearly revenue and 1000+ employees.
SENIOR ENTERPRISE ACCOUNT EXECUTIVE
RollWorks a division of NextRoll
01.2022 - 03.2024
- Achieved 165% of sales goal, generating $1.9 million in revenue as top three account executive in 2023.
- Closed largest deal in company history at $834,000 TCV, finishing 2022 at 340% of goal.
- Negotiated high-value contracts with Fortune 500 legal teams while managing transactional deals.
- Collaborated with C-suite executives and directors throughout sales cycle to drive strategic initiatives.
- Conducted onsite meetings with prospects and enterprise accounts to influence buying committees.
- Navigated complete sales cycle through discovery, multithreading, and strategic solutioning.
- Promoted to enterprise account executive within 10 months due to outstanding performance.
VP BUSINESS DEVELOPMENT & SALES
Honeycomb Credit
Pittsburgh, USA
02.2020 - 01.2022
- Increased sales by 340% YoY, the average deal size by 50%, and expanded market from 9 to 22 states.
- Increased sales revenue by 365% over two years.
- Reduced sales cycle time 30% by establishing and implementing formal sales process.
- Interviewed, hired, trained, and managed eight AE and SDR employees, fostering a high-performing sales team.
SENIOR ACCOUNT EXECUTIVE/PRODUCT SPECIALIST
Jetpack Workflow
Pittsburgh, USA
02.2017 - 02.2020
- Exceeded quota by 180% in 2017 and sustained 160% of quota in 2018 and 2019.
- Generated 42% of total revenue YoY, achieving highest yearly sales in company history.
- Collaborated with sales operations, marketing, and engineering teams to develop and enhance product offerings.
Education
Bachelor of Science - Business Administration, Marketing
Northeastern University
Boston, MASkills
- AI utilization for efficiency
- CRM and enterprise solutions
- Sales optimization strategies
- Consultative selling techniques
- Contract negotiation skills
- Cross-functional collaboration
- Networking and relationship building
- Deal qualification
- Executive communication
- MEDDPICC approach
- Experience with Claude, Gemini, Google Studio, and ChatGPT
Timeline
SENIOR ENTERPRISE ACCOUNT EXECUTIVE
BlastPoint
09.2025 - Current
Senior Enterprise Account Executive
Gladly
04.2024 - 09.2025
SENIOR ENTERPRISE ACCOUNT EXECUTIVE
RollWorks a division of NextRoll
01.2022 - 03.2024
VP BUSINESS DEVELOPMENT & SALES
Honeycomb Credit
02.2020 - 01.2022
SENIOR ACCOUNT EXECUTIVE/PRODUCT SPECIALIST
Jetpack Workflow
02.2017 - 02.2020
Bachelor of Science - Business Administration, Marketing
Northeastern University