Harald’s Curious Corner is where curiosity meets connection.
Harald chases that question with a guest, gathers perspectives from voices across the industry, and then steps back to reflect on what it all means. The show unfolds like a story arc, part exploration, part roundtable, part reflection, blending imagination with analysis.
The result: trusted insights, meaningful conversations, and forward-looking takeaways that shine a light on where learning is headed next.
In this episode, JD Dillon (https://www.linkedin.com/in/jddillon/), author of The Frontline Enablement Playbook (https://www.td.org/product/book--the-frontline-enablement-playbook/112602), shares why frontline employees need a fundamentally different approach to learning, enablement, and performance support. He explains why traditional training often clashes with the realities of frontline work, how L&D teams can connect their efforts to operational outcomes, and why the goal should be helping people become capable and confident on the job.
We also discuss why frontline managers are critical to performance. JD explains how operational pressure shapes their priorities, why corporate programs often break down at the manager level, and how enablement teams can build stronger support around real workflows. They explore frontline technology, learning in the flow of work, local culture, continuous listening, and why making a manager’s job easier can unlock better employee and business outcomes.
Some curious takeaways:
Connect frontline enablement directly to operational and business outcomes
Design support around the realities and priorities of frontline managers
Build learning into the workflow instead of pulling people away from the job
Episode highlights:
(00:00) Welcome to Harald’s Curious Corner
(01:40) 2.7 billion: 80% of the workforce is frontline
(02:34) Why L&D overlooks the frontline workforce
(06:27) Why it's so hard to support frontline workers
(09:57) Labor hours and the franchise challenge
(11:34) Business models that invest in frontline execution
(14:44) The "enshittification" of customer experience
(17:18) Proving top-line value to CFOs and CEOs
(20:43) Stop saying "learning" to your stakeholders
(31:31) The book's 12 authentic frontline stories
(34:35) The frontline hierarchy of needs
(38:49) Why frontline managers are the most important people
(55:11) "I want spandex, not concrete": building tech for frontline
(1:04:41) Magic wand: three things to eradicate and replace
Connect with the guest:
JD Dillon on LinkedIn: https://www.linkedin.com/in/jddillon/ (https://www.linkedin.com/in/jddillon/)
Explore The Frontline Enablement Playbook: https://www.td.org/product/book--the-frontline-enablement-playbook/112602 (https://www.td.org/product/book--the-frontline-enablement-playbook/112602)
Follow me on the following sites:
Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ (https://www.linkedin.com/in/haraldovera/)
Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/ (https://www.linkedin.com/newsletters/6901795950403186688/)
29 Sept 2026
Rethinking the Role of Customer Education in the AI Era
Customer education has spent years fighting to prove it belongs in strategic conversations. AI may finally force the issue.
In this episode, I’m joined by Danielle Evans from Sendoso, Monica Walsh from Klaviyo, Ashley DeKerlegand from Quickbase, Talya Reynolds from ClearCo, and Ben Love from Jupiter Learning for a practitioner-led conversation about where customer and partner education is heading.
A big theme emerged from the discussion: education creates more value when it stops behaving like an order-taking function. That means starting with the customer’s problem rather than the request for another course, then showing how learning connects to outcomes the wider business cares about.
AI changes what teams can produce and how quickly they can produce it. The more interesting question is what we do with that capacity. As content becomes easier to create, judgement, empathy, and a deep understanding of the learner become more valuable.
Some curious takeaways:
Start with the customer’s problem before deciding whether training is actually the answer
Connect education to meaningful business outcomes without losing sight of the learner
Use AI to remove repetitive work while protecting the human judgement that makes learning valuable
Episode highlights:
(00:00) Welcome to Harald’s Curious Corner
(08:12) Where customer education should live
(12:38) Looking beyond the training request
(16:35) Starting with the business problem
(20:15) Thinking like a growth leader
(24:02) Moving customer education beyond support
(28:49) Connecting content to customer outcomes
(32:14) When the traditional LMS falls short
(33:02) How adaptive learning can create demand
(39:19) Knowing what to delegate to AI
(46:41) What AI should actually automate
(53:01) Will AI mean smaller teams
Connect with the guest:
Danielle Evans on LinkedIn: https://www.linkedin.com/in/daniellemevans/ (https://www.linkedin.com/in/daniellemevans/)
Explore Sendoso: https://www.sendoso.com/ (https://www.sendoso.com/)
Monica Walsh on LinkedIn: https://www.linkedin.com/in/monica-sindwani/ (https://www.linkedin.com/in/monica-sindwani/)
Explore Klaviyo: https://www.klaviyo.com/ (https://www.klaviyo.com/)
Ashley DeKerlegand on LinkedIn: https://www.linkedin.com/in/ashley-dekerlegand-60760289/ (https://www.linkedin.com/in/ashley-dekerlegand-60760289/)
Explore Quickbase: https://www.quickbase.com/ (https://www.quickbase.com/)
Talya Reynolds on LinkedIn: https://www.linkedin.com/in/talyareynolds/ (https://www.linkedin.com/in/talyareynolds/)
Explore ClearCo: https://www.clearcompany.com/ (https://www.clearcompany.com/)
Ben Love on LinkedIn: https://www.linkedin.com/in/benlove26/ (https://www.linkedin.com/in/benlove26/)
Explore Jupiter Learning: http://www.jupiterlearning.co.uk/ (http://www.jupiterlearning.co.uk/)
Follow me on the following sites:
Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ (https://www.linkedin.com/in/haraldovera/)
Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/ (https://www.linkedin.com/newsletters/6901795950403186688/)
22 Sept 2026
Learning at GoDaddy: Experimentation, AI, and Human Skills
What happens when a learning and development team has to evolve as quickly as the technology and business around it?
Cammy Wood (https://www.linkedin.com/in/cammywood/), Global Director of L&D & Engagement at GoDaddy (http://www.godaddy.com), shares how her role grew from supporting sales training to shaping enterprise-wide learning, leadership development, onboarding, and skills enablement. She explains how GoDaddy uses experimentation, pilots, social learning, and learner communities to connect L&D with business performance.
We also discuss AI’s changing role in L&D. Cammy explains why learning teams must use AI, learn AI, and train others to use it while protecting proprietary information and keeping human judgement involved. They explore personalised learning, learning in the flow of work, dynamic SharePoint playbooks, manager accountability, and the soft skills organisations will need as AI becomes more common.
Some curious takeaways:
Start with the business outcome and work backward to the learning need
Use pilots and experimentation to learn quickly and iterate quickly
Meet learners in their time zones and create opportunities for social connection
Episode highlights:
(00:00) Welcome to Harald’s Curious Corner
(01:47) Building GoDaddy’s sales training programme
(03:26) How Cammy’s L&D role evolved
(06:09) Connecting learning to business performance
(08:56) GoDaddy’s align, connect, and grow strategy
(16:44) Making global learning feel personal
(21:56) Learning in the flow of work
(27:50) Why L&D must teach AI
(30:15) Balancing AI exploration with security
(32:17) AI as an enabler for learning
(37:21) Growing the Learning Connect community
(40:17) Creating shared language through team training
(42:16) The future skills of discernment and prioritization
(45:30) Why learning needs more lab work
(47:42) Keeping human judgement in the work
Connect with the guest:
Cammy Wood on LinkedIn: https://www.linkedin.com/in/cammywood/ (https://www.linkedin.com/in/cammywood/)
Explore GoDaddy: http://www.godaddy.com (http://www.godaddy.com)
Follow me on the following sites:
Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ (https://www.linkedin.com/in/haraldovera/)
Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/ (https://www.linkedin.com/newsletters/6901795950403186688/)
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