Sergio T. Orlando
Enterprise Account Executive/ SaaS Consultant
Atlanta,GA
Summary
Dynamic sales and marketing leader with over 8 years of experience driving SaaS sales, digital transformation, and strategic marketing initiatives. Skilled in developing and evaluating sales strategies, creating high-impact marketing assets, and optimizing AI-driven workflows. Proven ability to collaborate with cross-functional teams to refine AI systems, craft campaigns, and deliver data-driven results for C-level stakeholders. Adept at building playbooks, customer journeys, and sales frameworks to accelerate business growth.
Overview
8
8
years of professional experience
Work History
Founder & Technology Consultant
Orlando Advisory Group, Ltd.
Atlanta, GA
04.2023 - Current
- Developed sales and marketing strategies for B2B SaaS and public sector clients, creating onboarding playbooks and customer journey maps that improved client adoption by 30%.
- Collaborated with global consulting networks to evaluate ECM solutions, providing actionable insights to refine AI-driven content automation workflows for enterprise clients.
- Designed go-to-market strategies and pricing models for U.S. education and government sectors, supporting Deloitte-led initiatives with targeted campaign development.
- Delivered market intelligence and solution-fit analysis, aligning product strategies with organizational priorities to accelerate time-to-value.
Specialty Sales Account Executive
Hyland Software
Westlake, OH
04.2022 - 04.2023
- Secured a $1.45 M three-year SaaS contract by leveraging data-driven ROI analysis and C-suite engagement.
- Boosted qualified pipeline growth by 25% through optimized Salesforce CRM and LinkedIn Sales Navigator campaign frameworks.
- Partnered with AWS channel allies on mutual-deal campaigns, enhancing prospecting channels and streamlining AI/ML-driven contract procurement.
- Achieved 80% retention via structured stakeholder–engagement plans and campaign performance analysis.
Account Sales Associate, Specialty Sales
Hyland Software
11.2020 - 04.2022
- Designed 15+ persona-driven outreach campaigns with A/B testing, increasing conversion rates by 25% through tailored segmentation and messaging.
- Created sales-enablement assets (interview guides, qualification frameworks), reducing lead-to-opportunity time by 50%.
- Streamlined procurement cycles by 20% via partner collaboration, boosting campaign efficiency and onboarding.
Enterprise Account Development Representative
Alfresco Software
Atlanta, GA
12.2018 - 11.2020
- Generated $40 M in enterprise pipeline revenue using Outreach, HubSpot, and Salesforce.
- Pioneered a LinkedIn Sales Navigator outreach campaign, raising engagement by 60% and developing customer journey frameworks.
- Built five vertical-based qualification questionnaires, enhancing pre-sales efficiency by 50%.
Lead Development Representative
Alfresco Software
Atlanta, GA
01.2018 - 12.2018
- Ran discovery meetings with C-level executives, aiding a major enterprise deal via strategic account mapping.
- Mastered outbound prospecting with email campaigns and social outreach, driving lead gen across corporate and government sectors.
Education
Master of Business Administration -
Johnson & Wales University
Providence, RIBachelor of Science - Financial Services Management
Johnson & Wales University
Providence, RISkills
- SaaS/PaaS solution selling
- AI workflow evaluation
- Campaign development
- Sales playbook creation
- Customer journey mapping
- Executive relationship management
- CRM tools (Salesforce, HubSpot)
- Pipeline management & lead qualification
- Revenue growth & strategic planning
- Cross-functional collaboration
- Market research & competitive analysis
- MEDDIC framework
- Analytical & presentation skills
- Sales enablement
- Sales strategy
- Business development
- Operations management
- Team building
- Product roadmaps
- Market Knowledge
- Customer acquisition
Accomplishments
- Led three high-impact marketing campaigns at Hyland Software, securing enterprise migration contracts.
- Generated $2 M+ ARR at Hyland by hitting 120% of quota through targeted sales strategies.
- Built scalable sales playbooks at Orlando Advisory, slashing onboarding time by 30%.
- Optimized AI-driven content workflows with global consultancies, boosting system accuracy.
- Founded Orlando Advisory Group, driving 20% annual revenue growth via digital marketing and partnership agreements.
Quote
In the business world, the rearview mirror is always clearer than the windshield.
Warren Buffett
Timeline
Founder & Technology Consultant
Orlando Advisory Group, Ltd.
04.2023 - Current
Specialty Sales Account Executive
Hyland Software
04.2022 - 04.2023
Account Sales Associate, Specialty Sales
Hyland Software
11.2020 - 04.2022
Enterprise Account Development Representative
Alfresco Software
12.2018 - 11.2020
Lead Development Representative
Alfresco Software
01.2018 - 12.2018
Master of Business Administration -
Johnson & Wales University
Bachelor of Science - Financial Services Management
Johnson & Wales University
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