Kerry Heilskov
@kerryheilskov.bsky.social
Director of Sales Training and Enablement, Absorb LMS | Leadership, Training, and Development | Sales Enablement and
Industry Trends
Industry Trends
Big news from the Gong team that I’ve been waiting for! You know how “Ask Anything” lets you pull insights from a single sales call? Well, Gong is rolling out The Big Ask... and this changes everything. Soon, we’ll be able to ask anything across the entire platform. 🧵
December 22, 2025 at 2:55 PM
Big news from the Gong team that I’ve been waiting for! You know how “Ask Anything” lets you pull insights from a single sales call? Well, Gong is rolling out The Big Ask... and this changes everything. Soon, we’ll be able to ask anything across the entire platform. 🧵
Integrating the Together mentoring platform into our LMS was one of those “exciting on paper, complicated in practice” moments. We leaned on transparency, yes, but it was really about inclusion. Every decision and everyone impacted were in the loop... and that's essential!
December 17, 2025 at 2:58 PM
Integrating the Together mentoring platform into our LMS was one of those “exciting on paper, complicated in practice” moments. We leaned on transparency, yes, but it was really about inclusion. Every decision and everyone impacted were in the loop... and that's essential!
Can you believe 2026 is almost here? Time really does fly... and it’s the perfect moment to start thinking about what’s next for L&D. Luckily, this report from our Absorb team (with our friends at Together Software!) has some great insights into the future of learning and development.
See what’s next in learning & development
Thank you for being a subscriber to the Learning Prism. We started a year ago and now we’re here - with over 20k of you reading and excited to find out what’s next in learning.
www.linkedin.com
December 16, 2025 at 6:16 PM
Can you believe 2026 is almost here? Time really does fly... and it’s the perfect moment to start thinking about what’s next for L&D. Luckily, this report from our Absorb team (with our friends at Together Software!) has some great insights into the future of learning and development.
Recently attended the Gong Empower Workshop and I’m still thinking about the Operational Maturity Navigator they introduced! 🛠️ It’s a tool where you plug in your role, products, and goals... and it literally maps out what you should be doing daily, weekly, and quarterly to drive results.
December 15, 2025 at 4:42 PM
Recently attended the Gong Empower Workshop and I’m still thinking about the Operational Maturity Navigator they introduced! 🛠️ It’s a tool where you plug in your role, products, and goals... and it literally maps out what you should be doing daily, weekly, and quarterly to drive results.
Matthew Reeves, CEO of Together, recently shared his thoughts on the human side of learning and why it's so important for upskilling efforts. Too many companies treat upskilling as just a compliance issue, but when given real support, it a major growth opportunity.
Five questions with: Matthew Reeves
In this edition of “Questions With…” Matthew Reeves, CEO of Together, an Absorb company, shares why the human side of learning is essential for successful
www.talentcanada.ca
December 9, 2025 at 3:08 PM
Matthew Reeves, CEO of Together, recently shared his thoughts on the human side of learning and why it's so important for upskilling efforts. Too many companies treat upskilling as just a compliance issue, but when given real support, it a major growth opportunity.
We often have an image of leaders as authoritative, confident, and decisive, never showing signs of weakness or uncertainty. Yet research suggests that humility is often a better sign of strong leadership.
#Leadership #Humility
#Leadership #Humility
Why Humble Leaders Tend to Be the Most Effective Leaders, Backed by Considerable Science
Don't think you have all the answers? If you want to be a great leader, that's a good thing.
www.inc.com
December 8, 2025 at 2:13 PM
We often have an image of leaders as authoritative, confident, and decisive, never showing signs of weakness or uncertainty. Yet research suggests that humility is often a better sign of strong leadership.
#Leadership #Humility
#Leadership #Humility
If skills are the new currency, why don't more companies invest in upskilling and development? It isn't for companies to provide training for new hires. Companies need to make learning a part of their day-to-day operations to stay ahead of industry-wide changes.
December 5, 2025 at 4:02 PM
If skills are the new currency, why don't more companies invest in upskilling and development? It isn't for companies to provide training for new hires. Companies need to make learning a part of their day-to-day operations to stay ahead of industry-wide changes.
I could pretend there was just one insightful moment at Gong Celebrate '25… but honestly? All of it was insightful! Hearing directly from the founders really shifted things. Their message was loud, clear, and genuinely exciting: Gong is becoming a revenue enablement platform.
December 2, 2025 at 4:02 PM
I could pretend there was just one insightful moment at Gong Celebrate '25… but honestly? All of it was insightful! Hearing directly from the founders really shifted things. Their message was loud, clear, and genuinely exciting: Gong is becoming a revenue enablement platform.
When we introduced Gong, the learning curve was long. And honestly, that was by design. My biggest fear was that people would see it as “Big Brother”: a tool for monitoring instead of empowering. So instead of saying, “Here’s Gong, go use it,” we took the slow, intentional route. 🧵
December 1, 2025 at 4:25 PM
When we introduced Gong, the learning curve was long. And honestly, that was by design. My biggest fear was that people would see it as “Big Brother”: a tool for monitoring instead of empowering. So instead of saying, “Here’s Gong, go use it,” we took the slow, intentional route. 🧵
I spend a lot of time talking about leveling up... but that doesn't happen in a vacuum. It happens because I get to work with people who truly show up for each other! I’m also incredibly thankful for how this team continues to welcome new people with open arms. Happy Thanksgiving!
November 26, 2025 at 3:35 PM
I spend a lot of time talking about leveling up... but that doesn't happen in a vacuum. It happens because I get to work with people who truly show up for each other! I’m also incredibly thankful for how this team continues to welcome new people with open arms. Happy Thanksgiving!
Transparency sounds easy… until you’re actually in a moment where people are anxious, things are changing quickly, and everyone is looking for answers you don’t fully have yet. During the Together acquisition, this became very real for all of us. 🧵
November 24, 2025 at 4:20 PM
Transparency sounds easy… until you’re actually in a moment where people are anxious, things are changing quickly, and everyone is looking for answers you don’t fully have yet. During the Together acquisition, this became very real for all of us. 🧵
One of the very first things we did after Together joined Absorb was to give their team Absorb email addresses. It might sound small, but it made a big difference. Suddenly, they were included in all-company town halls, team updates, and even fun events like trivia and social contests. 🧵
November 18, 2025 at 4:40 PM
One of the very first things we did after Together joined Absorb was to give their team Absorb email addresses. It might sound small, but it made a big difference. Suddenly, they were included in all-company town halls, team updates, and even fun events like trivia and social contests. 🧵
So happy to announce that Absorb was recently named a Leader in The Forrester Wave™: Learning Management Systems and Experience Platforms, Q4 2025. The report called out Absorb’s focus on innovation, customer enablement, and community. And those are three things that I see come to life every day!
Absorb Software Named a Leader and Top-Ranked in Strategy Category in Learning Management Systems and Experience Platforms by Independent Research Firm
Absorb Software has been named a Leader in The Forrester Wave™: Learning Management Systems and Experience Platforms, Q4 2025.
www.absorblms.com
November 17, 2025 at 4:13 PM
So happy to announce that Absorb was recently named a Leader in The Forrester Wave™: Learning Management Systems and Experience Platforms, Q4 2025. The report called out Absorb’s focus on innovation, customer enablement, and community. And those are three things that I see come to life every day!
We often assume salespeople are only motivated by money. And yes, money matters, but it’s rarely the whole story. For some, the true motivator was recognition. The top sellers aren’t just chasing goals. They’re serving the customer first.
November 11, 2025 at 3:56 PM
We often assume salespeople are only motivated by money. And yes, money matters, but it’s rarely the whole story. For some, the true motivator was recognition. The top sellers aren’t just chasing goals. They’re serving the customer first.
I recently stepped into the role of Director of Sales Training & Enablement, and it’s had me reflecting on something I’ve learned the hard way: training alone doesn’t scale. Early in my career, Sales Training felt purely human. 🧵
The Journey from Sales Training to Sales Enablement Director
I recently stepped into the role of Director of Sales Training & Enablement, and I am so excited for this new journey! Going down this path has had me reflecting on my career, how I got here, and what Enablement truly is. When I first stepped into this space, I assumed Sales Training (teaching reps
www.linkedin.com
November 10, 2025 at 3:37 PM
I recently stepped into the role of Director of Sales Training & Enablement, and it’s had me reflecting on something I’ve learned the hard way: training alone doesn’t scale. Early in my career, Sales Training felt purely human. 🧵
People often assume sales is all about the money. And yes, of course that matters! But here’s what I’ve learned over my career: money is rarely the real motivator. From the very beginning, my coaching style has been about looking beneath the surface. 🧵
November 4, 2025 at 3:01 PM
People often assume sales is all about the money. And yes, of course that matters! But here’s what I’ve learned over my career: money is rarely the real motivator. From the very beginning, my coaching style has been about looking beneath the surface. 🧵
A couple of weeks ago, I attended Gong Celebrate in Austin, and wow…so much to unpack! What stood out most to me wasn’t just the cool innovations (though yes, the AI agents are impressive 👀), it was watching teams work smarter together.
Celebrate '25 | The AI Powered Revenue Era.
Join us at Celebrate '25 - the conference where the cutting-edge revenue leaders, operators, and sellers come together to shape the future of go-to-market.
www.gong.io
November 3, 2025 at 6:51 PM
A couple of weeks ago, I attended Gong Celebrate in Austin, and wow…so much to unpack! What stood out most to me wasn’t just the cool innovations (though yes, the AI agents are impressive 👀), it was watching teams work smarter together.
Just read an Inc.com roundup on mentoring, discretion, and networking. Reminded me how much leadership is about curiosity, patience, and timing. Sometimes the best guidance is asking the right questions, giving space, and letting others take the next step themselves.
How Do I Mentor a Very Timid Employee?
... and two other tricky workplace dilemmas.
www.inc.com
October 31, 2025 at 2:10 PM
Just read an Inc.com roundup on mentoring, discretion, and networking. Reminded me how much leadership is about curiosity, patience, and timing. Sometimes the best guidance is asking the right questions, giving space, and letting others take the next step themselves.
This really made me pause. Most of us don’t follow leaders blindly, but how often do we pause to ask if our support is aligned with principles, not just personality? Loyalty isn’t given, it’s earned, and tested every day.
When you follow a leader, consider what would lead you to withdraw your support.
If the answer is nothing, your integrity is in jeopardy. Our highest loyalty belongs to principles, not people.
No leader deserves unconditional love. Commitment is earned through character.
If the answer is nothing, your integrity is in jeopardy. Our highest loyalty belongs to principles, not people.
No leader deserves unconditional love. Commitment is earned through character.
October 30, 2025 at 1:16 PM
This really made me pause. Most of us don’t follow leaders blindly, but how often do we pause to ask if our support is aligned with principles, not just personality? Loyalty isn’t given, it’s earned, and tested every day.
You know that moment when AI starts feeling like a teammate?
That’s what’s happening at companies using Absorb’s AI-powered LMS.
AI isn’t replacing humans. It’s freeing them to do the work that requires context, care, and creativity.
The future isn’t humans or AI. It’s humans with AI.
That’s what’s happening at companies using Absorb’s AI-powered LMS.
AI isn’t replacing humans. It’s freeing them to do the work that requires context, care, and creativity.
The future isn’t humans or AI. It’s humans with AI.
October 28, 2025 at 2:00 PM
You know that moment when AI starts feeling like a teammate?
That’s what’s happening at companies using Absorb’s AI-powered LMS.
AI isn’t replacing humans. It’s freeing them to do the work that requires context, care, and creativity.
The future isn’t humans or AI. It’s humans with AI.
That’s what’s happening at companies using Absorb’s AI-powered LMS.
AI isn’t replacing humans. It’s freeing them to do the work that requires context, care, and creativity.
The future isn’t humans or AI. It’s humans with AI.
Gamification isn’t Candy Crush. It’s a performance booster. Absorb LMS turns badges, leaderboards, and quests into real skill and engagement wins. Geotab’s results show learning can be fun, sticky, and actually move the needle.
LMS Gamification: 8 real examples, proven best practices
LMS gamification isn’t just points and badges. Discover 8 real examples and best practices that actually improve learning in Absorb LMS.
www.absorblms.com
October 27, 2025 at 1:23 PM
Gamification isn’t Candy Crush. It’s a performance booster. Absorb LMS turns badges, leaderboards, and quests into real skill and engagement wins. Geotab’s results show learning can be fun, sticky, and actually move the needle.
There's a big difference between hands-on leadership and micromanaging. Hands-on leadership is about showing up where it matters and shaping the way work actually gets done. It’s not about controlling every move. What’s the most memorable “hands-on” moment you’ve seen from a leader?
The Surprising Success of Hands-On Leaders
Leadership theory suggests CEOs should focus on high-level issues such as strategy and resource allocation. These authors challenge this conventional wisdom by spotlighting CEOs who dive deep into day-to-day execution rather than hovering at the strategic level. By exploring best practices at Amazon, Danaher, RELX, and Toyota, they argue that top-performing companies thrive because of leaders who
go.upcontent.com
October 23, 2025 at 1:30 PM
There's a big difference between hands-on leadership and micromanaging. Hands-on leadership is about showing up where it matters and shaping the way work actually gets done. It’s not about controlling every move. What’s the most memorable “hands-on” moment you’ve seen from a leader?
If mentoring wasn’t on your 2025 bingo card, it should be! At Absorb, we’ve built mentoring right into our LMS with Together, making it easy to connect people in ways content alone can’t through structured leadership coaching, peer upskilling, or even casual coffee chats.
Introducing mentoring and coaching within Absorb LMS: Your complete learning system
Drive engagement and retention with a strategic learning system that includes mentoring with flexible matches, workflow integrations, and AI personalization.
www.absorblms.com
October 21, 2025 at 4:09 PM
If mentoring wasn’t on your 2025 bingo card, it should be! At Absorb, we’ve built mentoring right into our LMS with Together, making it easy to connect people in ways content alone can’t through structured leadership coaching, peer upskilling, or even casual coffee chats.
If I had to convince a new sales director that sales enablement is more than just managing a tech stack, here’s what I’d say. 🧵
October 20, 2025 at 3:31 PM
If I had to convince a new sales director that sales enablement is more than just managing a tech stack, here’s what I’d say. 🧵
According to a recent survey, 77% of respondents say they’ve experienced burnout on the job. Sadly, this statistic isn't really surprising. I've even experienced burnout at certain points in my career. But what really makes me happy is how we're trying to tackle this issue at Absorb. 🧵
Beating burnout in the workplace: It's a matter of life and death
A Statistics Canada survey found 21 per cent of employed Canadians experience "high or very high levels of work-related stress."
calgaryherald.com
October 14, 2025 at 3:13 PM
According to a recent survey, 77% of respondents say they’ve experienced burnout on the job. Sadly, this statistic isn't really surprising. I've even experienced burnout at certain points in my career. But what really makes me happy is how we're trying to tackle this issue at Absorb. 🧵