Katie Ainslie

Building Tomorrow’s Capabilities Today | $2B+ Revenue Impact

katie.ainslie110@gmail.com | linkedin.com/in/katieainslie110 | Boston, Massachusetts, US

Selected Achievements

· 48% revenue growth (2020–2025) through scalable enablement, onboarding, and learning programs aligned to Go-To-Market, product marketing, and business operations priorities.

· Digital Product Training Framework: Increased sales productivity by 20% and improved $1M+ deal velocity through strategic messaging and product positioning aligned with customer needs.

· Pipeline Palooza: Drove $49M+ deals, while enhancing cross-functional collaboration and stakeholder engagement (Director+).

· Sales Leader University: Achieved 75% 1:1 coaching adoption in one quarter, embedding MEDDICC, sales execution frameworks, to strengthen sales performance and consistency.

· Ascend: 4-day global event focused on outcome-based selling; resulted in $30.2M pipeline and 29% YoY bookings growth, integrating marketing strategies, customer insights, and storytelling.

Experience
Manager, Learning & Development, Enablement | Iron Mountain | November 2020–September 2025

· Lead a global creative team responsible for designing, developing, and delivering sales skills and leadership
development programs for 1,000+ sellers and sales managers globally.

· Drove 48% revenue growth (2020–2025) via scalable sales enablement, onboarding and learning aligned to go-to-market strategies.

· Managed multiple projects and competing priorities through rigorous planning, problem-solving skills, and
stakeholder influence to sustain delivery excellence.

· Championed AI-enhanced dashboards enabling continuous improvement cycles, connecting program data to KPIs, user needs, and performance outcomes.
· Designed and executed key programs including:

· Digital Product Training Framework: 20% increased sales productivity, increase in $1M+ deals

· “Pipeline Palooza”: Resulted in $49M+ deals in 2025, increased customer engagement (Director+).

· “Winning as One”: Increasing engaged accounts by 115% and booked revenue by 22% through targeted
enablement and learning programs.

· “Sales Leader University” with performance management and talent management frameworks—driving 75% adoption of structured 1:1s in one quarter—while developing ongoing learning programs and job aids, including Sales Competencies, MEDDICC and Consultative Selling, to embed continuous development.

· Led “Make Commercial Excellence a Great Place to Work” (Employee Engagement & Culture)

· Designed, developed, and facilitated a tiger team of cross-functional employees to provide a psychologically safe environment to share feedback.

· Implemented various initiatives across the organization resulting in significant improvements across all areas identified to help with talent management.

Instructional Designer, Sales Enablement | Iron Mountain | January 2018–November 2020

· Partnered with Onboarding owner to design and deliver scalable onboarding and training programs globally.

· Cutting ramp time by 32% for 455 hires across 43 countries in year one.

· Created Sales Leader Digest, translating data and coaching tips into clear, accurate communication improving leadership alignment and reliability.

· Proven collaboration skills with Sales, Marketing, and Product leadership to conduct needs assessments, discuss our gap analysis to align training strategy with revenue goals, ensuring programs drove both new business and customer retention.

· Ability to lead agile, blended global learning delivery, including self-paced, virtual, and in-person formats, working with regional market teams to ensure alignment and feedback; drove Ascend 2022 pipeline growth ($30.2M, 29% YoY bookings).

· Developed and implemented sales systems, driving adoption of AI-enabled tools (Mindtickle, Clari, 6Sense, WalkMe) to improve pipeline analytics, increase learner engagement, and accelerate revenue growth.

· Designed and executed key programs including:

· “Ascend”: A 4-day in-person event (in 5 regions) focused on using Outcome-Based Selling with our products: $30.2M pipeline, 29% YoY bookings growth

· “Super Sales Friday”: just-in-time resources and weekly training that boosted sales knowledge, kept sellers and sales leaders up to date on what customer’s were facing and how Iron Mountain could help solve their challenges, and increase confidence engaging customers during COVID-19.

Content Designer, Sales Enablement | Iron Mountain | February 2016 – January 2018

· Attention to detail with content creation for high-impact knowledge assets, playbooks, pitch decks, and competitive battlecards that improved win rates by and increased rep confidence in customer conversations.

· Translated complex product and industry insights into clear, actionable messaging that shaped deal strategy and accelerated pipeline growth.

· Optimized content ecosystem and workflow organization, cutting search time and ensuring accuracy and consistency across sales teams.

· Developed executive-level training presentations and user support materials for high-value deals, reinforcing brand credibility and customer trust.

Education

Manager Development Program | Iron Mountain | 2020

Instructional Design Certificate | Associate for Talent Development | 2019

BA Graphic Design/Letterform | University of Massachusetts | 2011

Tools & Platforms

Other: Enablement Analytics | Google Cloud | Microsoft Office Suite | OMG Sales Assessments | Baker Fuel IQ