In the season finale of The Enablement Edge, hosts Steve and Amber chat with Stephanie Middaugh, Founder & CEO of Phoenix GTM Consulting, about where to succeed in enablement in 2025.

Together, they tackle the industry's current challenges, including burnout and exhaustion among professionals, while highlighting the need to sustain passion and empathy in these roles. Stephanie shares actionable strategies for navigating market uncertainties and organizational obstacles, emphasizing the importance of prioritizing skill-building over task-focused activities and looking to what is actually within your control.

The discussion also explores Stephanie's book, Elevate and Optimize: Your Enablement Maturity Journey, which provides practical guidance on advancing enablement functions and setting achievable goals. Stephanie shares her insights into effective maturity models, the current and future impact of AI on enablement, and the transformative potential of a well-aligned enablement strategy. Her advice inspires listeners to stay focused on their enablement objectives and drive meaningful change within their organizations.

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Guest Bio

Stephanie Middaugh is a seasoned expert in revenue enablement and sales operations, known for her innovative approach to training and process improvement. She is currently a CSM with Luster, a cutting-edge AI sales practice and upskilling solution that is revolutionizing how go-to-market teams learn and practice. However, Stephanie is also the Founder & CEO of her own business, Phoenix GTM Consulting.

Most recently, Stephanie was the Head of Global GTM at Pinecone. With a career spanning leadership roles at Zoom, Divvy Inc., DataStax, Alteryx, and Sage, she has consistently built scalable enablement frameworks supporting global sales teams. Passionate about fostering community and delivering impactful programs, Stephanie continues to be a thought leader in the enablement space.

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Guest Quote

“People are tired, exhausted, and burnt out. But that passion is still burning. We want to help. So we're still going to be there.

Enablement as a profession is still going to get these initiatives, trainings, and everything [else] through. We're still going to be bought into helping our reps succeed and seeing the business move forward.

Even though it kind of goes through these ups and downs and ebbs and flows, enablement is going to be here for a while, and it's the companies that know how to properly leverage it that are going to see the results at the end of the day.”

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Time Stamps

00:00 Episode Start

4:45  How Stephanie defines enablement

6:38 Facing burnout in 2025

9:56  Where is all this pressure coming from?

12:50  Moving foward despite uncertainty

16:13 Focus in on what you can control

18:20 Elevate and Optimize: Your Enablement Maturity Journey

24:37 Does your enablement team have to be large to be mature?

28:11 Transformational enablement

31:40 On the Edge

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Links

• Connect with Stephanie Middaugh on LinkedIn
• Read “Elevate and Optimize: Your Enablement Maturity Journey”
• Check out Phoenix GTM Consulting
• Check out Luster
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic

In this episode of The Enablement Edge, hosts Steve and Amber are joined by Sally Ladrach, Director of Enablement at SavATree, a full-service tree, shrub, and lawn care company with more than 100 locations across the US and Canada.

The topic for today is how enablement teams can leverage agile methodologies found in product and marketing to enhance their own adoption and impact. Sally discusses the ways this type of framework focuses closer on the end user and iterative development to build more intentional solutions. She emphasizes the importance of involving stakeholders early in the process to ensure that what you're building truly meets their needs, thus enhancing adoption and, ultimately, driving business impact.

Sally also shares valuable insights on how to prioritize tasks that will deliver the most significant outcomes and tips for maintaining agility without losing sight of long-term goals. She also highlights the necessity of a data-driven approach and how agile principles can protect against wasted effort on non-adopted solutions. Tune in to discover how an agile framework can revolutionize your enablement strategy and drive tangible results.

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Guest Bio

Sally Ladrach is the Head of Enablement at SavATree, where she leverages over a decade of experience in sales enablement to drive impactful training and development initiatives. With a strong background in data-driven strategies, she focuses on enhancing team performance and collaboration across various departments. Previously, she served as the Revenue Enablement Manager at Thoughtbot, where she successfully implemented agile methodologies to improve learning and engagement. Passionate about fostering growth, Sally also advocates using storytelling in enablement practices to create meaningful connections.

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Guest Quote

“In enablement, I can't tell you how many times I've seen teams and maybe even done a little bit of this myself in the past. You work on that six-month rollout of whatever, you put it out there, ta-da, and then nothing happens.

People don't use it. Maybe, it wasn't designed with the end user in mind. But then you can't even have that impact, right? If your solution for whatever it is isn't being adopted. So that was kind of the genesis of how I started thinking about agile and enablement.

Obviously, I'm not the first person to think that agile is a great way to work, but the nature of enablement is that we are building solutions and agile at its core is about building user-centric solutions that are adoptable and solve problems.”

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Time Stamps

00:00 Episode Start

03:45 Welcome Sally

04:25 What is SavATree?

06:45 The most important thing enablers can do to ensure success

09:05 Today's topic: Agile enablement

16:25 Outcomes over output

19:20 You don't have to be perfect

25:20 Agile enablement in action

28:40 Where do charters fit in?

32:05 First steps to implement agile enablement

33:30 On the Edge

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Links

• Connect with Sally Ladrach on LinkedIn
• Check out SavATree
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic

On this episode of The Enablement Edge, Steve and Amber are joined by Ashton Williams, Director of Slack Enablement at Salesforce. Ashton shares the success story of Slack AI and how her team led a momentous kickoff amidst strenuous circumstances.

Faced with tight deadlines, executive transitions, and mounting pressure, Ashton shares how her team focused their efforts, aligned leadership with consistent buy-in, and leaned into the pivots. She also goes into detail on how they decided to format their kickoff with sales leader sessions, industry-focused webinars, certifications, and live pitches across three global regions in the same week.

What resulted from her and the team’s efforts was not only a huge boost to morale at the start of the year, but high and lasting sales success for a product that has continued to grow. The story highlights the importance of alignment and data-driven decisions in enablement functions, showcasing how strategic execution can have impactful outcomes in a changing business environment.

Perfect for enablement professionals yearning for both inspiration and practical knowledge, this episode provides an edge in enhancing their craft. The fusion of witty anecdotes and profound discussions invites listeners to engross themselves in the transformative power of enablement, making it a not-to-be-missed episode for those looking to sharpen their strategic edge.

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Guest Bio

Ashton Williams is a seasoned professional in the field of enablement and strategic programs, currently serving as the Director of Slack Enablement at Salesforce. With a strong focus on building high-performing teams, Ashton has leveraged her diverse background in sales and leadership to enhance organizational effectiveness.

Prior to her role at Slack, Ashton gained valuable experience in various sales enablement positions, including a significant stint at Ada, an AI-powered customer experience platform. There, she was responsible for establishing the enablement function from scratch, emphasizing the importance of data-driven decision-making and iterative learning.

Ashton’s educational background and commitment to continuous improvement have made her a respected figure in the enablement community. She is Co-Chair of The Enablement Squad’s Leadership Lounge and actively shares insights on best practices in sales training and employee engagement. Her passion for fostering collaborative environments has positioned her as a leader in driving strategic initiatives within tech organizations.

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Guest Quote

“This ended up being Slack's first ever in person kickoff. Morale, retention, feeling connected to the team, attrition, all of those things, like we saw impact there. The sentiment was just one of absolute inspiration. And we made a bet and it really paid off in both what we call overall AEs hitting quota. But also to see that new product that we focused on be our absolute darling. It has continued to be the feature of our QBRs. It's continued to be the thing we double down on. It has been the thing we're putting more investment on the roadmap in because we're moving it. And also, you know, that's always lovely to see that customers love the things we build.”

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Time Stamps

00:00 Episode Start

01:10 Today’s Topic

03:30 Welcome Ashton

04:00 The most important thing enablers can do to ensure success

05:10 Setting the stage: Slack's Q1 of 2024

07:40 Why it was critical to enable every part of the business

09:20 How did Ashton do it?

11:30 Focusing all your efforts on a single motion

15:25 Sometimes you need to lean into the pivots

18:25 Leverage the data you have

19:30 Deeper into program specifics

23:00 You can't do it alone

26:10 The results of Ashton's efforts

29:40 Lessons learned

31:35 On the Edge

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Links

• Connect with Ashton Williams on LinkedIn
• Learn more about Slack AI
• Check out Salesforce
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic

In this episode of The Enablement Edge, Steve and Heather sit down with Jen Bullock, an expert in the field of enablement who has worked with industry giants like ADP, Motorola, TransUnion, and Forrester.

The topic today is the art of crafting a winning enablement structure. Jen highlights the critical roles needed for success and how to strike the perfect balance between strategic foresight and tactical execution, shedding light on the evolving concepts of program management, centers of excellence, and the rising trend of fractional enablement professionals.

Amidst rapid technological change, Jen stresses the importance of not forgetting the basic principle of connecting to the customer journey. And as it relates to hiring freezes, the trio discuss the need for enablement professionals to do away with simply onboarding and instead provide ongoing ‘everboarding’ for employees. They stress the importance of roles that might be overlooked such as technical enablers and even field coaches, exploring their future in the era of AI.

Packed with actionable advice and insightful discussions, whether you're a seasoned leader or just starting your journey in enablement, this episode is a must-listen for anyone eager to refine their enablement strategy.

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Guest Bio

Jennifer (Jen) Bullock is a seasoned professional in the fields of marketing and sales enablement, with a robust career spanning several leadership roles in notable organizations. She has cultivated a reputation for her strategic approach to aligning marketing and sales efforts with customer needs. Her work emphasizes the importance of creating sales efficiency through innovative platforms and metrics analysis, ensuring that sales teams have the necessary tools and knowledge to engage effectively with clients.

Most recently, Jen was a Principal Analyst specializing in Revenue Enablement Strategies at Forrester, one of the most influential research and advisory firms in the world. In this role, Bullock worked with senior executives to deliver actionable intelligence, transformative frameworks, and expert guidance. Bullock's work with Forrester built upon her rich background with organizations such as ADP & TransUnion.

Bullock's expertise also extends to implementing learning management systems that facilitate tailored learning paths for sales personnel. In addition to her corporate achievements, Jen Bullock is recognized for her contributions to the marketing landscape through innovative digital strategies that have driven substantial returns on investment. Her ability to integrate technology solutions into marketing efforts has positioned her as a leader in the industry, making significant strides in enhancing customer engagement across various sectors.

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Guest Quote

“You always hear the stat of: ‘Customers do 70, 80, 1000 percent of their own learning before they even engage with the salesperson.’

I don't think that that's a matter of they don't want to engage with the salesperson. What they want is an objective understanding of what need you're filling.

So the more that a salesperson is adapting and understanding what that customer is looking for, that makes the better salesperson.” – Jen Bullock

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Time Stamps

00:00 Episode Start

01:08 Today’s Topic

04:00 Welcome Jen

04:14 The most important thing enablers can do to ensure success

05:30 Be strategic, not reactionary

07:38 Why charters are so valuable

12:30 Comparing the different enablement models

15:40 The trend of fractional team members

20:35 Back to the basics

21:55 Training vs. Learning

25:45 How priorities have shifted for organizations

27:55 Which roles matter most

31:40 The future of the field coach

33:30 Who is an ideal enablement leader?

38:40 Showing off your skills online

40:35 On the Edge

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Links

• Connect with Jen Bullock on LinkedIn
• Find Jen’s articles
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic

In today’s episode of The Enablement Edge, hosts Steve Watt and Heather Cole interview Kunal Pandya, VP of Global Revenue Enablement at Corsearch, and Founder & CEO of Sales Velocity Labs.

Kunal is a seasoned expert in global revenue enablement, and he helps to explore how enablers can transform their roles and prove their strategic value within any organization. Arguing that the current perception of enablement as a cost center has made lasting impacts on the industry, Kunal emphasizes the importance of not shying away from the data.

Kunal also provides practical advice for enablers seeking to elevate their function within their organization, underlining the importance of benchmarking and obtaining leadership buy-in before implementing enablement programs. By demonstrating how different levels of competence and performance can result in measurable revenue gaps, enablers can justify their initiatives and establish credibility.

Amidst all of the data and metrics, Kunal does remind all of us that the people are what matter most in enablement. Empathy and human relationships are as foundational as anything else, especially as AI changes the way we work.

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Guest Bio

Kunal Pandya is the Vice President of Global Revenue Enablement at Corsearch and the Founding CEO of Sales Velocity Labs. With a rich background in championing sales enablement, Kunal has dedicated years to transforming the perception and impact of enablement functions in organizations.

Kunal holds over 20 years of experience in the technology and high-growth SaaS industry. Throughout his career, he has built revenue impacting enablement functions and strategies for some of the fastest growing global tech companies, while at the same time being recognised as one of the top twenty enablers in the world.

Kunal founded Sales Velocity Labs to elevate the effectiveness of worldwide sales enablement, to impact revenue by a minimum of 15%.

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Guest Quote

“The perception of enablement has been such that companies have laid off hundreds, if not thousands of enablers globally. This has to change. Because we cannot have enablement in that position. We know where it belongs, we just have to prove it. We have to make it believable.”

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Time Stamps

00:00 Episode Start

01:08 Today’s Topic

03:00 Welcome Kunal

03:54 The biggest challenge facing enablement today

06:26 Why showcasing ROI is difficult, but necessary

09:55 Which four categories should enablers be measuring?

14:46 How to separate your impact from factors beyond your control

20:41 The path to continuous improvement

24:22 Highlighting the value of data

26:46 Kunal's advice for enablement leaders

32:00 On the Edge

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Links

• Connect with Kunal Pandya on LinkedIn
• Check out Corsearch
• Check out Sales Velocity Labs
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic

In this episode, Steve Watt and Amber Mellano are joined by Nicole Ward, Senior Director of Revenue Enablement at OneSource Virtual (OSV), to learn why she joined the organization as their first enablement hire and how she and the team found so much success.

Nicole is an industry expert and thought leader who joined OSV after a decade of managing an award-winning team of enablement innovators at Citrix. Today, you’ll hear all about her remarkable achievements with OSV. Her highlights include a substantial reduction in new hire ramp time and time-to-first-opportunity, along with impressive improvements in deal sizes and win rates that she attributes to her strategic approach and collaboration with various business functions.

Throughout the interview, Nicole emphasizes the importance of obtaining executive buy-in and stakeholder alignment early in the process to ensure success. She advocates for focusing on a few key pillars and avoiding the temptation to "boil the ocean” when first starting. Nicole's emphasis on leveraging data, maintaining ongoing communication, and building cross-functional relationships demonstrates how critical these elements are for effective enablement.

By sharing her experience and practical advice, Nicole provides a clear roadmap for building a robust enablement function that can adapt and thrive amid organizational change.

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Guest Bio

Nicole Ward is a passionate and technology-forward global revenue enablement leader with over 14 years in the field. She is currently the Senior Director of Revenue Enablement at OneSource Virtual after a decade of managing an award-winning team of enablement innovators at Citrix.

Nicole believes that a successful enablement program must be centered around empathy and be inclusive of all customer-facing teams. Nicole is a bridge builder who will work cross-functionally to drive productivity and ensure satisfaction with enablement programs. She is data-driven and process-oriented with a laser focus on bringing enablement into the context of actual opportunities with CRM integrations.

On the personal side, Nicole is a multi-tasking mom who resides in London, Ontario, Canada with her husband James and two small children. She enjoys cooking, cycling, traveling, and she dreams of pursuing a sommelier certification someday. Fun fact: Prior to starting her family, Nicole was one of Canada's early lifestyle "influencers" and launched Canada's first conference targeted to style influencers in 2013.

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Guest Quote

“In enablement, we are bridge builders, and we are serial collaborators. It's all about connecting with people across the organization to understand what they do, how can I learn from them, what can they learn from me, how can I support them, what are their goals, can I attach myself to their goals, especially if they were key stakeholders in enablement. It's all about building your internal network.”

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Time Stamps

*(04:31) Nicole's key to enablement

*(05:56) Coming in as the first enablement hire

*(07:52) When do you know that you're ready for the next opportunity?

*(09:56) Building out the enablement function before day one

*(13:01) How to leverage the greater team around you

*(15:50) The data behind Nicole and OSV's success

*(18:40) Why you need to partner with your fellow business functions

*(22:06) Being thrown into the deep end

*(28:25) Nicole's advice for others

*(30:45) On the Edge

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Links

• Connect with Nicole Ward on LinkedIn
• Check out OneSource Virtual
• Connect with Steve Watt on LinkedIn
• Connect with Amber Mellano on LinkedIn
• Check out Seismic
• OneSource Virtual Revolutionizes Revenue Enablement
• Citrix Enhances Content Discovery
• The State of AI in Enablement Report