Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.
Introduction
I’ve yet to meet an enablement leader who hasn’t wrestled with the politics, the shifting priorities, and the delicate dance of stakeholder buy-in.
In fact, when I asked dozens of top enablement professionals about their most persistent challenges, one theme shot straight to the top: stakeholder management and alignment.
Or, more precisely, the lack of it.
Why is it so critical?
Because even the sharpest enablement strategy will stall if you can’t get the right people engaged, aligned, and moving in the same direction.
And yet, as I explored in my deep dive on the top sales enablement challenges, stakeholder management remains one of the hardest muscles to build – especially when you’re navigating change resistance, cross-functional silos, and “whack-a-mole” requests from every corner of the business.
One of the contributors to that article, Elena Giunta, captured the risk clearly:
“Communication breakdowns between different departments, such as sales, marketing, and customer support, can lead to misunderstandings, conflicting strategies, and a lack of cohesion in the overall sales enablement process.”
It’s a familiar picture: your roadmap looks strong on paper, but in the absence of stakeholder engagement and trust, execution unravels, teams pull in different directions, and momentum quietly dies.
So, to understand how the most respected enablement leaders actuallynavigate this and which stakeholder management skills are helpful, I turned to those who’ve been in the trenches – who’ve faced the friction, felt the stall-outs, and still found ways to move the business forward.
Alex Bedford – GTM Enablement Lead
Alicia Heagle – Revenue Enablement Lead
Christopher Kingman – VP of Sales Transformation
Darwin Singson – Revenue Enablement Lead
Dave Turis – Director of Sales Enablement
Dawn O’Rourke – Senior Director, Revenue Enablement
Georgia Watson – Enablement Leader, Australia & New Zealand
Giorgia Ortiz – Senior Director, Global Revenue Enablement
Jill Guardia – Senior Vice President, Revenue Enablement & Operations
Lisa Hammack – Director, Global Field Enablement
Meganne Brezina – Head of Enablement
Sam Moody – Global Director of GTM and CS Enablement
Sam Wener – Senior Director, Sales Enablement
Samantha Thompson – Director, Global Sales Enablement
Sheryl Buscheck – Director, Global Revenue Enablement
Timea Bara – VP, GTM Enablement
Umar Gill – Vice President, Commercial Enablement

In the sections that follow, you’ll find their most practical, hard-won stakeholder management best practices – organised into the themes and sub-themes that kept cropping up again and again in their stories.

Building relationships and trust
Every successful stakeholder management process starts, and often succeeds or fails, with relationships.
Before you can align on strategy or drive results, you need to be seen as a credible, empathetic ally – someone stakeholders want to work with, not just someone they have to.
Building these relationships takes time, emotional intelligence, and a willingness to adapt your approach to the people who will (hopefully) become your partners.
Empathy and emotional intelligence
Empathy is the quiet force that shapes lasting relationships with stakeholders.
The most effective enablement leaders make space for honest conversations and show up for their stakeholders, even when there’s no immediate agenda.
It’s also the surest way to build trust, a keystone for engaging cross-functional partners and earning long-term buy-in.
Alicia Heagle, the Revenue Enablement Lead at an SF-based payment operations platform, captured this reality perfectly:
“One key lesson I’ve learned is that trust doesn’t happen overnight, and not everyone will be ready to align immediately.
It takes time, a willingness to learn their communication style, multiple conversations, and sometimes having a tough discussion.
By investing in the relationship early, I’m setting us up for long-term collaboration and alignment.”
Samantha Thompson, the Director of Global Sales Enablement at a cybersec platform, described her approach, where she always makes the first move and starts building relationships from day #1:
“I prioritise identifying and building relationships with my stakeholders as soon as I start my new role.
This could be joining standing calls, shadowing existing projects, and/or setting up recurring 1:1s.
I make a point to be present for them even if I’m not ready to begin tackling a project because I’m in the midst of onboarding.
This shows that I understand the success of enablement is contingent upon relationships and that I’m there to work with them.”
Samantha goes even further, building safe spaces for her stakeholders, particularly front-line sellers who may otherwise feel overlooked or unsupported:
“I always give my stakeholders space to vent without judgment.
This is especially powerful for sales teams as they often feel like they have no say and are basically told to “shut up and sell” for lack of a better phrase.
By giving my stakeholders space to have open, candid conversations, they can work through their frustrations in real time.
The simple act of giving someone space has helped me build a number of strong relationships and get buy-in because my teams know I’m always there to hear them out and support them.”
She also shared how great an effect this can have on entire sales organisations:
“Their favorite part?
Sometimes I am able to influence the C-suite and make changes to programs, and it creates a virtuous cycle of helping the sales teams feel seen and heard in ways they haven’t previously.
My favorite part?
I’ve seen this completely turn around sales teams. This is a deceptively small gesture that has massive impacts on culture and performance.”
She summed it up perfectly in a short, sweet, and very candid sentence:
“In short, show your stakeholders you give a sh*t.”
Sam Wener, the Senior Director of Sales Enablement at the company behind the world’s most popular prototyping software, framed the emphatic side of enablement as being aware that everyone is buried under an avalanche of their own tasks, responsibilities, problems, and stress and that stakeholder expectations are often completely unknown:
“Teams are leaner than ever and moving faster than ever, so ensure you act with empathy and recognise that no one has the time, so help them understand why helping you and giving their time matters.”

Adapting to stakeholder styles
Empathy opens the door, but building trust means stepping through it and meeting stakeholders in the way they prefer to communicate and collaborate
Every partnership brings its own quirks, with some stakeholders wanting every detail, others preferring a quick summary and clear next steps.
Recognising these preferences and responding in kind can make all the difference.
Alicia Heagle has seen this play out time and again. She says:
“A common mistake is trying to push your working style on others – it’s not all about you!
As a former AE, I naturally lean toward speed and decisiveness, but I’ve learned that different stakeholders operate differently.
For example, if someone prefers a methodical, detail-oriented approach, I make the effort to adapt my communication, slowing down, clarifying the ask, and providing more context.”
Sam Wener also pointed out how important it is to find out exactly what it is that resonates with stakeholders, especially those who are outside the sales organisation:
“For effective stakeholder management, it’s so important to tell a story and align it to the thing that stakeholder cares about.
If it’s someone you’re trying to align with outside of your organization (ie. reporting to different c-suite), it’s important to align to company priorities – whatever alignment you’re looking to drive, should be connected to a mutual company priority.”
Sam Moody, the Global Director of GTM and CS Enablement at a company behind one of the most popular HR platforms, makes a habit of asking stakeholders directly how they want the partnership to work:
“When building new relationships, I ask, ‘How do you want our partnership to look and work?’
This question helps you assess a stakeholder’s understanding of your enablement function, their expectations from your team, and their preferred collaboration style.”
She also listens for the language that resonates with each stakeholder group, picking up on patterns in how leaders communicate with their teams:
“Communicating in a way that resonates with stakeholders builds rapport, increases credibility, and builds trust. This alignment ensures stakeholders feel heard and understood, which is key to gaining their buy-in and support for future initiatives.”
Dave Turis, the Director of Sales Enablement at a company equally famous for its motorcycles and its electric pianos, also mentions tailored communication and value framing as one of his best practices.
Flexibility in approach and communication turns empathy and understanding into action.
Stakeholders notice when you make the effort to adapt, and it sets the stage for genuine partnership.

Establishing credibility
Empathy and interpersonal skills can take you and your enablement team only so far.
Sooner rather than later, you’ll need to start building trust on your results as well.
Stakeholders look for evidence – clear signals that your work is moving the business forward and that you’re committed to sharing progress, challenges, and outcomes along the way.
Jill Guardia, the Senior Vice President of Revenue Enablement & Operations at one of digital learning powerhouses, relies on steady, transparent communication to keep trust growing.
She keeps every leadership layer in the loop, making sure there are no surprises and alignment remains strong:
“If I’m in constant communications with my key stakeholders—sales leadership, CX leadership, product leadership and quite frankly the full Exec team—there aren’t surprises and there is full support and alignment.”
For Meganne Brezina, the Head of Enablement at a leading enterprise SaaS Management platform, credibility grows when you share insights that matter to the business. She surfaces trends and actionable intelligence, positioning enablement as a strategic partner:
“When you surface trends in deal health, gaps in messaging, or behavioural insights from tools like Gong or Salesforce, you become more than just a ‘trainer’—you elevate yourself into a trusted advisor to various stakeholder groups.
Executives crave actionable intelligence that helps them lead better and make faster decisions.”
Lisa Hammack, the Director of Global Field Enablement at an API-first analytics platform, puts measurement at the centre of her approach. She ties every initiative to company goals and tracks the impact, building confidence through data:
“By tying to their OKRs, you can ensure that what you are working with is going to have a meaningful impact on the business.
A second piece of that is that you measure everything.
This includes both leading and lagging indicators.
If you are able to measure the impact of your initiatives, you build confidence from your leadership team and earn the right to work alongside them to identify gaps and opportunities.”
Credibility grows through a steady rhythm of showing up, sharing what you learn, and backing up your story with results that matter to the business.

The contributors are very clear: when both internal and external stakeholders know you’re present, listening, and reliable, you create the foundation for every future conversation and collaboration.
As trust gets more and more established, the next challenge is deeply aligning on what truly matters: setting priorities, defining success, and making sure everyone is moving in the same direction.
In other words…
Alignment with goals and strategic objectives
Building trust lays the groundwork, but real progress happens when everyone is pulling in the same direction.
According to the enablement leaders who helped me with this article, stakeholder alignment is a continuous process of surfacing priorities, defining what success looks like, and making sure every initiative supports the broader business strategy.
When enablement leaders get this right, they turn stakeholders into partners, and are far more likely to deliver long-lasting impact.
Understanding stakeholder priorities
Every effective partnership starts with clarity.
The most successful enablement leaders invest time up front to understand what matters most to each stakeholder – what they’re measured on, where they feel the pressure, and how enablement can help them hit their goals.
Christopher Kingman, the VP of Sales Transformation at the world’s leading consumer intelligence company, was very vocal about the importance of understanding what matters to the stakeholders, especially since many of them aren’t aware of how exactly enablement can help them:
“Start with stakeholder goals and priorities – Do some project stakeholder analysis to understand their roles, priorities, expectations, and the goals they need to meet.
Stakeholders may or may not be aware of how enablement can help, so clarifying their goals or how they are compensated or bonused matters.
By understanding their goals, you can position your strategy as a benefit to them.
Understanding their priorities helps you identify where they may need help first.”
He goes on to explain that it is essential to, then, translate those priorities and expectations into actual results that would help the stakeholders achieve their goals:
“Define what success looks like – Once you have their goals and priorities, work to understand what successfully meeting those would look like.
Although you should align enablement strategies to the broader organization, determine how the programs or work you do address their goals, and can meet their definition of success.
And to be clear, meeting their definition of success may not always align with meeting the goal.
Stakeholders may have a vision of how meeting that goal should look or how it should transpire.
Some may not have a preference and be satisfied with the goal being met.
Making the distinction and getting that information will help form how you engage with them, and how you articulate the value.”
Darwin Singson, the Revenue Enablement Lead at a pioneer in global pay transparency solutions, builds on something Christopher mentions – the need to understand how stakeholders’ goals fit with the company’s goals and how enablement can be the function to tie it altogether:
“Making sure you and your stakeholder are aligned to the same revenue producing goals.
If not, work to agree on your goals and directions.
Stakeholders should not feel they are a stakeholder but a partner working to achieve the same goal.
Stakeholder and/or their team should know they need to vet what is about to be released and agree to all released items.”
Meganne Brezina shares how she partners with stakeholders to drive alignment between their priorities, enablement efforts, and the organisation’s strategic objectives:
“Always align your efforts to the corporate objectives.
The fastest way to earn credibility and stakeholder support is to anchor your enablement initiatives in the business’s highest priorities.
This means going beyond functional goals to connect your work directly to what the executive team cares most about—whether that’s increasing win rates, accelerating pipeline velocity, or improving customer retention.
When stakeholders see that enablement is a lever to drive outcomes they’re measured on, they’re far more likely to engage and champion your work.
Alignment also serves as a north star, helping you make smart trade-offs and avoid pet projects that don’t serve the bigger picture.
Your efforts should be detailed in an enablement charter that is updated quarterly for continuous alignment and visibility.”
Sheryl Buscheck, the Director of Global Revenue Enablement at a network infrastructure leader, goes into even more details, singling out the VSEM planning model as a best practice for ensuring the goal alignment for everyone involved:
“What has worked best for me is utilising corporate and CRO goals to create an annual plan each year for Enablement to contribute to those goals.
I happen to love the VSEM planning model: Vision-Strategy-Execution-Metrics in which the ‘Execution’ piece details quarterly big-rock programmes to move specific metrics (e.g. grow pipeline, higher win rates, shorter sales cycles, higher ASP, etc.).
The most important part of the process is to review your draft plan with leaders, get feedback and ultimately come to a final agreed-upon plan.”
Georgia Watson, the Enablement Leader for Australia & New Zealand at one of the world’s biggest tech companies, suggests a very common-sense and practical way to build inroads into the organisation:
“Focus on stakeholders who have the most to gain—or lose—from enablement initiatives. Help them see the impact on themselves, their teams, and the business.
When your programs align with strategy, you naturally build strong allies.”

Of course, understanding stakeholder concerns and priorities and aligning to strategic goals is not just a phase that kicks off collaboration between enablement and its stakeholders.
It’s the groundwork.
And when done well, it naturally develops into…
Co-creation and early involvement
I wrote and re-wrote half a dozen introductions to this section about co-creation and early involvement.
In the end, I realised that the best way to introduce the topic and illustrate why enablement should act as organisational integrators, which nudge various stakeholders (sales, marketing, product, customer success, etc.) to move from parallel towards convergence, is to let Alex Bedford, the GTM Enablement Lead at a leading enterprise microsegmentation company, share a story from his personal experience:
“…One organisation I worked at had a culture of “Splendid Isolation” where the likes of sales, product marketing, engineering, field marketing, customer success, and sales enablement all interacted more or less independently, operating from each other, achieving only operational and tactical successes as a result.
When I started talking to leaders of these functions (most of whom had not spoken to an enablement professional before), they all articulated they had the same overarching goal of increasing sales in 2 solutions in particular.
I suggested we (enablement) lead a project where we all partner to strategically impact these shared goals.
This led to the curation of GTM Certification for sellers, where all functions were invited to contribute what they felt was valuable, but the enablement team was responsible for curation and held “final edit” rights.
Sellers had to complete the entire program, but it was streamlined and aligned with the existing sales process (sellers are stakeholders too, and this was important for them).
Sellers only became certified after they sent out a “digital pitch” using our new Digital Sales Room platform.
The outcomes were strategically significant…within one quarter pipeline of the first priority solution was up 34%, which continued to grow and convert over subsequent quarters (driven by certified sellers who had not had pipe in that solution before).
We repeated for the second solution with similar results.
These certifications were referenced on 3 subsequent earnings calls to Wall St!”
Darwin Singson also shared a story from his personal experience, to a similar effect:
“I worked with product managers to help me develop content for Persona, competitive, and GTM strategy training.
At first, they were resistant as it was more work for them.
I used Sales Leadership and CRO to convey the importance and provide me with the leverage I needed to speak to them about joint revenue goals.
I appealed to their goals that aligned to revenue and also spoke to CMO.
Long story short, I convinced them and they agreed they needed to do enablement.
CMO also realised that enablement content development was best done by product marketing and, going forward, all new product marketing hires and job descriptions had enablement as a primary function.”
Georgia Watson sees early involvement as a best practice that turns stakeholders into genuine advocates:
“Co-create.
Involve stakeholders early to gather input and co-design initiatives.
This surfaces concerns, uncovers insights, aligns goals, and turns contributors into advocates. Keep evolving together.”
Timea Bara, the VP of GTM Enablement at a leading legal ediscovery software company, echoes the importance of bringing internal stakeholders along from the very beginning, making sure you’re not just presenting problems, but also collaborating on solutions:
“The most important thing is to bring the stakeholders along the journey!
If we don’t involve them early, we might make assumptions that are not the right ones or not correctly prioritised.
The worst thing we can do is to only show problems instead of solutions.
Stakeholders need to see that we understand the issues and are able to think strategically, recommend interventions.
Sometimes the expectations of an outcome are very different for enablement vs stakeholders, so aligning on it early is crucial.”
Dawn O’Rourke, the Senior Director of Revenue Enablement at a platform for intelligent connectivity and automation, makes a very astute observation that meaningful co-creation happens in direct conversation, not just email chains or group announcements:
“Use 1:1s to gain input instead of mass emails—direct conversations lead to more meaningful feedback and stronger support.
Speak their language—tie initiatives to their goals (pipeline, revenue, ramp time, etc.).”
Giorgia Ortiz, the Senior Director of Global Revenue Enablement at the biggest equity management software company, starts with pointing out how important it is to communicate the scope of the collaboration with stakeholder co-creators:
“Making sure you share the context and journey with your stakeholders is important if you are looking for real buy-in and adoption.”
Giorgia goes on to stress the importance of listening to stakeholder feedback as a way to enable ongoing alignment, which also happens to be the next sub-theme.

Sustained alignment
As Giorgia puts it:
“Leaving space for modifications to your initial plan to incorporate valid stakeholder feedback is critical for any stakeholder management plan.
Creating programmes or initiatives in a vacuum because they look good on paper is a sure way to fail.”
Sustained alignment is a continuous rhythm, not a one-off achievement. It requires regular planning, reviewing, and adapting to keep everyone moving forward together.
Sheryl Buscheck highlights the importance of embedding alignment into the business cycle:
“You should do quarterly reviews of results from previous quarter, what is launching current quarter, and what is being built for next quarter (and see if leaders want to make any changes to the Q+1 plan).
The business rhythm of annual planning and quarterly review cycles ensures ongoing alignment, support and results/metrics that matter to revenue leaders.”
Umar Gill, the Vice President of Commercial Enablement at a global leader in industrial software, frames this as a Journey Management Concept where you:
“Create alignment through the inception, design, build process of a programme (for example sales learning masterclasses) but then most importantly, have a triple tiered launch process:
Initial leadership launch
First-line manager launch
Mass launch to key audiences, with a varied message – what, why, how, whats in it for them.”
This way, stakeholder alignment follows a very natural hierarchical progression, which ensures that it doesn’t peter out after the roll-out.
Dawn O’Rourke, on the other hand, focuses on continuous engagement, which sustains alignment through social sharing of success stories:
“Show results fast and often.
Focus on what matters most to stakeholders—lead with outcomes like adoption, engagement, and early wins, even before full revenue impact is visible.
Celebrate success stories—highlight reps or teams benefiting from your work, and link those to broader business goals.
Socialise your impact intentionally—start with senior leadership, then cascade wins down through the organisation.
Build champions—position leaders, project managers, and top performers as advocates.
At my company, Enablement has a standing place in QBRs to discuss what’s working and what’s not.”
In my experience, reinforcing alignment as programmes go on is absolutely vital for successful enablement.
It is one thing for all stakeholders to jump on board the alignment train following an invigorating collaborative session. It is a whole different thing to keep the train full and chugging along as planned.

Communication, collaboration, and feedback
If there’s a single thread running through every successful stakeholder relationship, it’s communication.
This is reflected in the insights my contributors shared – the most effective enablement leaders intentionally create open channels for dialogue, shape collaboration around real needs, and actively invite (and provide) feedback at every stage.
Frequent, focused, valuable communication
Consistent, purposeful stakeholder communication is the glue that holds stakeholder relationships together, but far too often, enablement departments fall back to the “updating mode” where they settle for sending out regular updates to leadership.
The best enablement leaders, instead, make sure every touchpoint adds value, keeps stakeholders engaged, and moves the work forward.
Meganne Brezina is clear about the pitfalls of the “updating mode” and how to avoid it:
“Even the best initiatives fall flat without ongoing, relevant communication.
Stakeholders are busy, and enablement can quickly become ‘out of sight, out of mind’ unless you proactively share progress, roadblocks, and impact.
Regular updates—tailored by audience—keep everyone aligned and build trust that you’re moving the needle.
It’s not just about frequency, though; it’s about focus.
Lead with data, stories, or quick insights that tie back to their goals.
Being smart about how you engage with various levels of leadership is smart too—depending on the size of the GTM team you are serving, consider weeklys with your front-line managers, monthlys with your VPs, and quarterly with your executives to report back on the metrics that matter.”
Meganne also emphasises the importance of surfacing insights that matter to senior leaders, something that I’ve also identified as one of the surest ways to become a strategic partner:
“Enablement sits at a strategic vantage point—close enough to the field to hear friction points and far enough to spot patterns across teams.
When you surface trends in deal health, gaps in messaging, or behavioural insights from tools like Gong or Salesforce and identify stakeholders to which these matter, you become more than just a ‘trainer’—you elevate yourself into a trusted advisor.
Executives crave actionable intelligence that helps them lead better and make faster decisions.
Sharing those insights proactively (not just when asked) demonstrates thought leadership and deepens your influence at the leadership table.”
Umar Gill highlights the need to use multiple communication mechanisms.
Whether it’s formal updates, informal check-ins, or layered launch communications, reaching stakeholders where they are (and in the way they prefer) keeps everyone engaged.
Dawn O’Rourke brings it back to the basics of transparency and momentum:
“Follow up after every touchpoint—recap decisions, clarify action items, and build momentum through transparency.”
Frequent, focused, and valuable communication ensures that every interaction helps stakeholders feel informed, valued, and confident that enablement is driving results that matter to them.
I’d personally add that communication is among the most neglected stakeholder management skills and that inferior communication is often the reason why even the strongest stakeholder management strategies fail in execution phase.

Setting clear roles and expectations
No stakeholder partnership thrives on guesswork.
Clarity about roles, responsibilities, and decision-making helps everyone move faster and with more confidence.
The best enablement leaders don’t wait for confusion to set in; they set expectations up front and revisit them as partnerships evolve.
Sam Moody makes this a habit from the very start:
“We shouldn’t assume that everyone knows how to partner with enablement effectively, especially given their varied previous work experiences.
Build a RACI for clarity (the source of truth for the partnership!), and find quick wins in shaping more efficient workflows.
By setting the tone for open communication and shared goals from the outset, you encourage a sense of ownership and transparency in the relationship.
This approach ensures stakeholders feel their needs and preferences are respected and integrated into the partnership.”
She goes further, emphasising the importance of formalising these agreements:
“Start by drafting a RACI based on your workflows and the way you typically collaborate with others/departments.
Once you’ve got something down, bring in your stakeholder(s) to validate it, discuss dependencies, and clear up any uncertainties.
This is key for gaining buy-in and making sure everyone’s aligned.
Having a RACI to refer to helps keep things from getting blurry and makes collaboration more effective.
It’s a simple way to set clear expectations, so everyone knows their role and nothing falls through the cracks.”
Christopher Kingman adds another layer, focusing on decision-making and leadership:
“In my experience, stakeholders want to be involved with initiatives, but don’t necessarily want to make all the decisions.
Once you identify priorities and what project success looks like, as you plan your work, at any decision point in your process, try to determine if you can make the best decision possible.
For any decision that could possibly go to your stakeholder, make the decision, and have a solid, ‘no regrets’ reason why you made it.
In your check-in’s with those stakeholders, present the path you have laid out, the decisions and justifications, and only present questions that absolutely need their voice.
And for those decisions they need to make, ensure you provide as much detail and context necessary so they can make the best possible decisions.
This will better position you as a leader, instil trust in your stakeholders that you are driving the initiative, and ensure the most critical decisions are brought to the right group.”
When everyone on the project team knows where they stand, collaboration becomes far easier – and it helps prevent the blame game if things don’t go as planned.

Conclusion
Stakeholder management is a living, ongoing practice that asks you to show up, listen, adapt, and deliver – over and over again.
The leaders who shared their stories here don’t claim to have all the answers, but they do agree on one thing: progress happens when you put people first and keep the business context in view.
Whether you’re building trust from scratch, navigating competing priorities, or keeping alignment alive through yet another change, remember: every conversation, every check-in, and every shared success builds the foundation for the next.
The most effective enablement professionals build partnerships that last.
If you’re struggling, you’re not alone.
Every leader quoted here has faced the same frustrations and found ways through.
Take what resonates, experiment with the rest, and keep the dialogue open.
In an industry that changes from day to day, that’s the real best practice.
I’d like to end things by thanking Alex, Alicia, Christopher, Darwin, Dave, Dawn, Georgia, Giorgia, Jill, Lisa, Meganne, Sam Moody, Sam Wener, Samantha, Sheryl, Timea, and Umar once again for sharing their insights!
By the way, they were also kind enough to share their insights about the biggest stakeholder management mistakes and how to avoid them.
