Tara Caligiuri
Bethlehem,PA
Summary
Strategic Account Executive with 9+ years of experience managing, retaining, and expanding enterprise B2B accounts across SaaS, HCM, payroll, and AI-driven platforms. Proven track record of achieving 95%+ retention, exceeding multi-million-dollar quotas, and driving revenue growth through renewals, upsells, and strategic account planning. Trusted advisor to executive stakeholders, known for consultative selling, QBR leadership, and maximizing customer lifetime value.
Overview
10
10
years of professional experience
Work History
Strategic Account Executive
Enable
01.2023 - Current
- Own and grow a portfolio of enterprise accounts with end-to-end responsibility for renewals, retention, and expansion.
- Consistently achieve 95%+ customer retention by proactively identifying risk, aligning solutions to customer goals, and driving measurable outcomes.
- Lead executive-level QBRs, translating performance metrics into strategic growth plans and expansion opportunities.
- Identify and close upsell and cross-sell opportunities within existing accounts, increasing contract value and long-term customer lifetime value.
- Partner cross-functionally with Customer Success, Product, and Leadership to ensure seamless onboarding, adoption, and renewal outcomes.
- Manage a $1M+ quota, leveraging Salesforce and Salesloft to forecast pipeline, track engagement, and deliver predictable revenue.
Senior Business Development Manager
CloudPay
01.2022 - 01.2023
- Built strategic relationships with enterprise and multinational organizations, aligning CloudPay’s global payroll solutions to complex business needs.
- Acted as a trusted advisor to key decision-makers, supporting long-term partnerships and solution adoption.
- Identified expansion opportunities within existing territories, driving a 10% increase in revenue through consultative engagement.
Enterprise Account Executive
Forethought AI
01.2021 - 01.2022
- Managed enterprise SaaS accounts, partnering with customers to implement Mutual Success Plans aligned to AI-driven operational goals.
- Drove revenue growth by identifying upsell opportunities and presenting tailored AI solutions to executive stakeholders.
- Built and converted a $1M+ pipeline by expanding relationships within the ideal customer profile (ICP).
- Collaborated closely with technical and customer success teams to ensure successful deployment and sustained customer satisfaction.
Enterprise Account Executive
Ascentis (UKG)
01.2020 - 01.2021
- Retained and expanded enterprise HCM accounts by presenting measurable ROI and aligning solutions to operational and strategic objectives.
- Led training sessions and post-sale enablement to drive adoption, usage, and renewal success.
- Improved client retention by 20% by incorporating customer feedback into solution strategy and execution.
District Sales Manager – Small Business Markets
Paychex
01.2020 - 01.2021
- Led and coached a team of 10+ HCM sales representatives, driving a culture of accountability, collaboration, and customer-centric selling.
- Developed a referral-driven growth strategy through partnerships with CPAs, branch leadership, and client advocates.
- Consistently exceeded district revenue targets while improving customer satisfaction and retention metrics.
Senior District Manager | Sales Executive
ADP
01.2016 - 01.2020
- Managed a portfolio of 150+ enterprise and mid-market accounts, focusing on retention, expansion, and long-term relationship growth.
- Achieved 206% of quota by delivering customized, value-based solutions aligned to client business objectives.
- Partnered with senior executives to present strategic account plans and drive multi-year customer commitments.
- Trained and mentored new sales professionals on consultative selling, account strategy, and executive communication.
Education
Master of Science - undefined
Drexel University
Bachelor of Science - undefined
East Stroudsburg University
Skills
- Strategic Account Management
- Enterprise Client Retention & Renewals
- Revenue Expansion & Upselling
- Strategic Account Planning
- Executive Stakeholder Engagement
- QBRs & Mutual Success Plans
- Consultative / Value-Based Selling
- Cross-Functional Collaboration
- Technology: Salesforce, Sales Navigator, HubSpot, Gong, ZoomInfo, Salesloft, Microsoft Suite
Timeline
Strategic Account Executive
Enable
01.2023 - Current
Senior Business Development Manager
CloudPay
01.2022 - 01.2023
Enterprise Account Executive
Forethought AI
01.2021 - 01.2022
Enterprise Account Executive
Ascentis (UKG)
01.2020 - 01.2021
District Sales Manager – Small Business Markets
Paychex
01.2020 - 01.2021
Senior District Manager | Sales Executive
ADP
01.2016 - 01.2020
Master of Science - undefined
Drexel University
Bachelor of Science - undefined
East Stroudsburg University