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HELLO, MY NAME IS

Ryan Kolofsky

SALES ENABLEMENT EXECUTIVE

rye2kolo@gmail.com​
239-357-9366
linkedin.com/in/ryankolofsky

About Me

I’m a sales and revenue enablement leader focused on helping teams reach their full potential and drive measurable revenue growth.

With firsthand sales experience and a proven track record backed by multiple references, I know what it takes to succeed and deliver real results. I’ve enhanced performance through strategic training, go-to-market plans, and operational improvements.

At my core, I’m a people-first leader who builds trust, listens closely, and develops talent. By blending sales methodologies with creative content and modern enablement, I drive lasting impact and measurable outcomes.

Agile sales enablement executive driving performance

Leverages expertise in training and development to empower sales teams, ensure knowledge transfer, and support corporate sales objectives.

Master of the sales process, executive leadership, sales methodology, adult learning, and process improvement.

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What I Do

I build revenue engines that scale people, process, and performance.

Revenue Performance
Elevate sales performance through strategic enablement, agile methodologies, and structured content that aligns execution with measurable revenue outcomes.
Team Development
Build high-performing revenue teams through leadership development, scalable onboarding systems, and continuous coaching frameworks.
Ramp Acceleration
Reduce time to first sale by 25 to 30 percent through tailored onboarding design, certification programs, and operational alignment across revenue teams.

An accomplished ultra marathon runner

My Experience

KnowBe4
2025 to 2026
Vice President, Revenue Enablement
  • Led global enablement across AEs, AMs, BDRs, and Customer Success
  • Drove adoption of sales process and certification programs across teams
  • Partnered with Sales, SE, and leadership on scalable readiness
Lightcast
Aug 2024 to Present
Director of Revenue Enablement
  • Reduced ramp time from 6 months to 5 weeks
  • Improved time to first sale by 35 percent
  • Increased renewal rates from 91 to 97 percent
hh2
Nov 2023 to Aug 2024
Senior Director of Sales Training and Enablement
  • Reduced ramp time by 30 percent
  • Launched Highspot and certification programs
  • Reduced Salesforce hygiene errors by 70 percent
Kalderos
Feb 2022 to Nov 2023
Senior Director of Sales Enablement
  • Improved ramp to first sale by 25 to 30 percent
  • Built 90 plus certification programs
  • Revamped pipeline review using Gong dashboards
StructionSite
Aug 2021 to Feb 2022
Director of Sales Enablement
  • Reduced AE ramp from 12 weeks to 4 weeks
  • Implemented LevelJump LMS and onboarding structure
  • Aligned sales and marketing content processes
TraceLink
Apr 2021 to Aug 2021
Director of Sales Enablement
  • Developed cross functional sales training initiatives
  • Strengthened messaging alignment with Marketing
FairWarning and Imprivata
Jan 2020 to Apr 2021
Director of Training and Enablement
  • Built competitive battle cards and objection frameworks
  • Improved sales alignment through structured process education
FairWarning and Imprivata
Jan 2019 to Jan 2020
Sales Enablement Officer
  • Directed SDR onboarding and ongoing training programs
MidAmerica Administrative and Retirement Solutions
May 2016 to Dec 2018
Director, Learning and Development
  • Implemented LMS and leadership development curriculum
  • Launched interactive internal training platform

Education

Bachelor of Communications
University of South Florida
Associate of Arts, Communications
St. Petersburg College
Certified DISC in the Workplace Facilitator
Everything DiSC®
Advanced AI Prompting Certification
University of South Florida

Awards

Outstanding Sales Support
Kalderos · 2022
Employee of the Month
Lightcast · 2024
MVP Award
FairWarning · 2021
MARS Employee of the Year
MidAmerica · 2017

Skills

%
Sales Enablement & Training
%
AI Tools and AI Sales Strategy
%
Sales Operations and GTM Planning
%
Employee Onboarding & Everboarding
%
Employee Development
%
Training Certificate Programs
%
Sales Stage Architecture & Strategy
%
Sales Methodology Training
%
SaaS Software Sales
%
Challenger Sales
%
Content Management Systems
%
Learning Management Systems
%
Leadership Training
%
Sales Methodology
%
Instructional Design
%
Project Management
%
Adult Learning
%
PMA, Hussle & Hard Hardworking Attitude

Tools

LMS, Enablement & Coaching
  • Highspot
  • Letter AI
  • Brainshark
  • LevelJump
  • Gong
  • Klue
  • LinkedIn Learning
  • SalesHood
CRM, Sales Engagement & Ops
  • Salesforce
  • HubSpot
  • Outreach
  • Salesloft
  • Gong Engage
  • Seismic
Content, Creation & Collaboration
  • Notion
  • Synthesia
  • Figma
  • Camtasia
  • Adobe Captivate
  • Adobe Creative Cloud
  • Descript
  • Articulate Storyline

Portfolio

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