Diana Ashton
St Louis,MO
Summary
Results-driven sales leader with a strong background in business development, client relationship management, and strategic sales within luxury travel, hospitality, and fundraising sectors. Proven success in penetrating new markets, securing high-value partnerships, and delivering tailored solutions for B2B and non-profit clients. Adept at managing full sales cycles, leveraging CRM tools for scalable outreach and retention, and elevating both revenue and brand prominence.
Overview
11
11
years of professional experience
Work History
Fundraising Specialist, Sales Development
Winspire
09.2024 - 05.2025
- Prospected and secured new business in the nonprofit fundraising space, offering luxury travel and high-end entertainment for charity auctions.
- Topped leaderboard in sourced leads two months consecutively through cold calling, personalized outreach, and multi-channel prospecting.
- Closed top-performing deals, expanding Winspire's footprint in higher education and foundation sectors.
- Advanced top-of-funnel success by overseeing a robust pipeline in HubSpot CRM, executing 35+ daily calls, and deploying automated email cadences to boost engagement and lead qualification.
Business Development Manager
Classic Vacations
10.2023 - 07.2024
- Fostered relationships with 300+ travel agency partners, delivering consistent repeat business.
- Accelerated sales by identifying new B2B opportunities and converting leads into long-term clients.
- Analyzed market trends and provided strategic insights to leadership.
- Represented the brand at trade shows and coordinated FAM trip logistics.
Regional Director, Fundraising & Sales
Inspirato for Good
07.2022 - 10.2023
- Drove $200K+ in nonprofit fundraising revenue within five months by partnering with 501(c)(3) organizations.
- Forged inaugural partnerships and strategic alliances with key nonprofit chapters and private schools, unlocking new opportunities with Boys & Girls Club of Hawaii, Cystic Fibrosis Foundation Greater Illinois, and other mission-aligned organizations.
- Crafted outbound messaging and sales enablement assets for the nonprofit sector, helping launch a new philanthropic arm and build lead generation from the ground up in Salesforce CRM.
- Ensured seamless donation fulfillment, including invoicing, donor communications, and compliance.
Remote Sales, Online Research & Content Writer
Freelance
01.2021 - 07.2022
- Spearheaded digital sales campaigns and created B2B/B2C content to boost client visibility and revenue.
- Reengaged lapsed lead lists with new campaigns, generating 1,500 qualified leads.
Business Development Manager
Unique Vacations, Inc. (Sandals & Beaches Resorts)
07.2018 - 12.2020
- Revitalized an underperforming inherited territory, achieving 30% growth through targeted outreach, account strategy, and consistent quota attainment supported by regional marketing plans.
- Built strong client pipelines via resort visits, in-agency cold calls, and event-based engagement to expand market presence and boost revenue.
Regional Trainer (Concurrent Role)
Unique Vacations, Inc.
07.2018 - 12.2020
- Designed and facilitated training for travel consultants via webinars, on-site workshops, and industry conferences, with attendee groups ranging from 20 to over 100 participants.
- Aligned training with brand goals, enhancing partner performance and brand consistency.
Distributor Sales Consultant
Sally Beauty Holdings
11.2017 - 07.2018
- Managed a book of 85+ salon accounts, increasing client retention and growing territory sales by 15% in a declining market.
- Partnered with manufacturers to launch new product lines and grow market share.
Executive Outside Sales Manager
The Tiger Hotel
03.2014 - 03.2015
- Marketed and sold event space, room blocks, and group packages for boutique luxury hotel.
- Secured new revenue by partnering with NCAA-ranked college programs and universities, and converting SMERF opportunities into booked business.
Skills
- CRM: HubSpot, Salesforce Tools: Google Workspace, Slack, MS Office
- Sales: Email Campaigns, Virtual Demos, Cold Outreach
Timeline
Fundraising Specialist, Sales Development
Winspire
09.2024 - 05.2025
Business Development Manager
Classic Vacations
10.2023 - 07.2024
Regional Director, Fundraising & Sales
Inspirato for Good
07.2022 - 10.2023
Remote Sales, Online Research & Content Writer
Freelance
01.2021 - 07.2022
Business Development Manager
Unique Vacations, Inc. (Sandals & Beaches Resorts)
07.2018 - 12.2020
Regional Trainer (Concurrent Role)
Unique Vacations, Inc.
07.2018 - 12.2020
Distributor Sales Consultant
Sally Beauty Holdings
11.2017 - 07.2018
Executive Outside Sales Manager
The Tiger Hotel
03.2014 - 03.2015
Bachelor of Science - Sports Medicine, Business Administration Minor
William Woods University
Education
Bachelor of Science - Sports Medicine, Business Administration Minor
William Woods University
Fulton, MOCore Competencies
- Revenue Growth & Market Expansion
- Top-of-Funnel Sales Strategy | Startup Vertical Execution
- High-Ticket Nonprofit Fundraising & Donor Partnerships
- Luxury Travel, Hospitality & Mission Driven Sales
- Client Acquisition, Retention & Engagement
- Key Account Growth & Territory Management
- Consultative & Solution-Oriented Selling
- CRM Optimization (HubSpot, Salesforce)
- Virtual Sales Presentations & Lead Nurturing
- Cross-Functional Collaboration & Event Strategy
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