Cailin Kearns
@cailinkearns
Senior program manager who turns complex SaaS onboarding into structured, empathetic learning that accelerates ramp and adoption.
United StatesWhat I'm looking for
I take the complicated and make it comprehensible—especially for technical field teams selling complex SaaS—because empathy and curiosity show up in every program design decision. I’ve spent 10+ years building learning programs that keep teams on track mid-acquisition while prioritizing the person going through the program.
At HashiCorp (an IBM Company), I’ve led global technical enablement and onboarding efforts, building a structured six-week, two-track Solutions Architecture onboarding curriculum that reduced ramp time by 50%. I’ve unified Solutions Engineering and Customer Success programs globally, driven cohort-based onboarding across Madrid and Bengaluru, and boosted mandatory learning completion from 12% to 91% in a single quarter through manager engagement and structured communications; I also curated centralized learning repositories and refined an AI-powered chatbot for on-demand learning at scale.
Experience
Work history, roles, and key accomplishments
Led operational strategy for worldwide field enablement and managed global webinar and knowledge-sharing programming. Owned SalesCast and Technical Knowledge Share end-to-end, achieved 95% satisfaction for Sales Kickoff breakout execution for 1,200+ attendees, and led Highspot to Seismic migration ahead of renewal deadline, saving $300K+.
Supported Solutions Architecture and Customer Success onboarding and evergreen enablement, then led global onboarding for Solutions Engineering, Customer Success, and Solutions Architecture. Built a structured six-week, two-track Solutions Architecture curriculum and reduced ramp time by 50%, while driving learning completion from 12% to 91% in a quarter.
Senior Enablement Manager - Solutions
Gem
Jan 2022 - Nov 2022 (10 months)
Owned technical enablement across the Revenue organization for 170+ teammates during a period of ARR growth from $15M to $33M over three quarters. Built product enablement programming, launched a Highspot instance, and developed technical job aids and competitive intelligence aligned to product releases.
Strengthened the global Sales Engineering organization through enablement, onboarding, communications, and mentorship. Partnered with SMEs to train on new Jamf product releases and planned and emceed virtual Sales Engineering Camp for 120+ global attendees.
Helped establish the Education Specialist team focused on K–12 needs and the technical complexities of synchronous and asynchronous learning. Drove technical demos and conversations with sales partners, consistently achieving or exceeding 100% quota.
Provided onsite and remote onboarding, configuration, and training for Jamf products to 150+ customers. Earned Highest Customer Satisfaction for Americas in 2018 and mentored new teammates.
Training & Development Specialist
Api National Service Group
Oct 2008 - Mar 2017 (8 years 5 months)
Built and managed new hire onboarding processes, including benefits, software application training, and company policy training. Developed training videos and job aids and facilitated instructor-led courses based on process and platform improvements.
Education
Degrees, certifications, and relevant coursework
University of Wisconsin–Green Bay
Bachelor of Arts, Mass Communications
Earned a B.A. in Mass Communications with an emphasis in Public Relations.
Haagse Hogeschool
Exchange Program, Communication Management
Completed a Communication Management exchange program in The Hague.
Tech stack
Software and tools used professionally
Availability
Location
United StatesAuthorized to work in
Job categories
Skills
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