How to improve your sales enablement maturity level

An enterprise SaaS GTM org sensed something was wrong. Deals were stalling. Reps were frustrated. Enablement programmes felt busy, but not effective.

The enablement team wasn’t slacking. They were shipping content, running training programmes, holding office hours. And still, something just wasn’t clicking.

So, they did something brilliant: They paused.

Rather, they intentionally stepped back and zoomed out to figure out if their sales enablement activities were truly helping reps win more deals (and faster).

That small decision kicked off a much-needed deep-dive into how its overarching enablement function operated, where it helped, and where it was inadequate:

• They conducted an honest audit of their current state and surfaced a lack of consistency across onboarding, manager enablement, and strategic content delivery.
• Go-to-market leaders spoke with reps and enablement specialists to uncover workflow blockers and pinpoint process gaps between tool access and field execution.
• Sales operations consolidated redundant platforms and adopted smarter AI-powered solutions that delivered content and coaching based on live pipeline context.
• Enablement then overhauled training programmes to include dynamic paths based on tenure, role, and product line complexity for better alignment with business objectives.
• Following this series of informed adjustments, based on intense scrutiny of its GTM operations, the team’s sales enablement programme ROI soared within weeks, thanks to stronger content usage, reduced onboarding times, and higher deal conversion rates.

This is just one example of go-to-market leaders recognising ‘The Way Things Are Done’ should evolve into ‘Work Smarter, Not Harder’ through identifying and taking action on issues, updating their approaches, and adopting AI-enabled technology to aid their enablement function (and other GTM teams).

It’s ideal for every business unit, inside and outside go-to-market, to take a step back every few months and audit what is and isn’t going well. As it relates to your sales enablement efforts, it’s worth asking yourself, “Is this working?”

If the answer is “Sort of” (or, worse, “Not sure”), it’s time for strategic adjustments and a change of course with your company’s sales enablement journey.

Put plainly, moving up the sales enablement maturity curve is the means to greater go-to-market consistency and impact: enabling systematic execution, measurable results, and stronger alignment across every GTM function.

After all, a widening go-to-market performance gap doesn’t just fix itself.

Knowing where your org stands on the sales enablement maturity model

If you never pause to take stock, you never know what’s working.

That’s why assessing your sales enablement maturity quarterly is a savvy move. It helps you detect where your enablement strategy has outgrown itself and where calculated upgrades and adjustments could unlock real GTM gains.

Once you know where you stand, you can zero in on what to change—and what to leave behind—as you evolve from reactive support function to performance-driving partner that provides reps and account executives a clear path to realising sustainable, predictable, and repeatable B2B sales success.

Our Go-to-Market Maturity Model breaks enablement (and all other business units in GTM) into four key stages: Reactive, Structured, Connected, and Strategic.

Your job? Figure out where you are, then start climbing to the next stage.

From Reactive to Structured

• Audit what content and training exists and whether reps actually use it.
• Replace one-off efforts with onboarding and campaign-ready frameworks.
• Define governance for how assets are stored, updated, and maintained.

Moving from Reactive to Structured requires getting organised: defining roles, standardising collateral and messaging, and giving your sales team a single, trusted source of truth for content, training, and plays. This is the ‘build-a-foundation’ phase.

From Structured to Connected

• Align training and assets to the sales process, not just product launches.
• Integrate enablement metrics into GTM dashboards to track utilisation.
• Reinforce key sales skills with ongoing training and manager coaching.

Levelling up from Structured to Connected is about alignment: embedding enablement into workflows, building cross-functional visibility, and using analytics to validate what’s landing. Think less ‘Distribute assets’ and more ‘Enable performance.’

From Connected to Strategic

• Create programmes that back big-picture goals, not just daily tasks.
• Use insight from data to refine which content and training matter.
• Equip managers to coach effectively and scale what works best.

The leap from Connected to Strategic is where enablement becomes a business lever: supporting B2B revenue growth, empowering sellers with AI sales enablement tools, and influencing outcomes across every sales funnel stage.

Moving up the different stages of the sales enablement maturity model

Once you’ve pinpointed your current stage, it’s time to act.

That doesn’t mean blowing everything up. Rather, it simply means choosing a few high-impact shifts to tackle every so often (monthly, quarterly—it’s up to you) that level you up without overwhelming your team. It also means ruthlessly prioritising based on what will drive the most value for sales reps and the business.

Questions that sales enablement leaders like you (and other trusted advisors in GTM) should ask before making any strategic or tactical changes include:

• Are sellers consistently using the sales messaging, content, and plays we’ve built, or are key resources and materials sitting untouched or buried in folders?
• Are our sales onboarding and training experiences measurably improving ramp time, or are new sellers still struggling to get up to speed quickly?
• Can I clearly tie sales enablement efforts to revenue growth or pipeline improvements, or is the connection still fuzzy or anecdotal and hard to assess?
• Do I know which assets and plays drive results at each stage of the sales cycle, or are we making assumptions without clear collateral usage data?
• How often are we refreshing sales training, brand positioning, and GTM assets, and does that cadence help or hinder sellers out in the field recently?
• Are frontline managers reinforcing critical skills in 1:1 sales coaching sessions, or is sales enablement falling off with reps after the initial rollout?
• Is our sales enablement function supporting sales strategies and strategic initiatives proactively, or do they react too late with content and training?

This kind of introspection takes time—and yes, it pulls you out of the day-to-day grind. But what you’ll get in return is a roadmap to greater sales enablement maturity, stronger cross-functional trust, and measurable business success.

By answering these Qs (among many others), your GTM org can:

Shift from reactive enablement efforts to a strategy that drives measurable business impact

Historically, enablement meant checking boxes and hoping for the best. Today, though, it’s (thankfully) more about backing every go-to-market move with data-driven insights and sales analytics that actually show what’s working.

If your enablement function still runs on gut feel, you’re behind and flying blind while your competitors are building clarity and control into their strategy.

Maturity means fewer fire drills and more purposeful planning with GTM metrics that tie enablement to results, like pipeline momentum and close rates.

Assemble an enablement team that consistently supports rep performance and execution

Getting the whole sales enablement team to operate and iterate around rep activity, behaviour, and needs requires the removal of silos within GTM and getting (and staying) in sync with the people who drive revenue every day.

You need enablement personnel who obsess over improving sales performance and know how to spot deficiencies and concerns before they become fires.

When sales enablement plays nicely with other functions in GTM, everything from training to tools to timing gets sharper, smoother, and way more useful.

Replace ad-hoc enablement with repeatable programmes that scale across the organisation

Your go-to-market org needs repeatable motions that make your sales enablement strategy at large stronger with every turn of the flywheel.

Consistency doesn’t happen overnight, but with feedback loops and a unified platform that everyone in GTM leverages daily and integrates with other essential tools, your team can move from doing more ‘stuff’ to running legit programmes that scale.

Operationalise sales enablement to make it leaner and smarter—that’s the goal.

Craft sales content and messaging that aligns with prospects’ needs and deal stages

Random assets and last-minute decks don’t cut it anymore (if they ever truly did). Your sales reps need pertinent, personalised content tailored around a deep understanding of where a given buyer is in their journey and what they care about.

Great GTM messaging speaks directly to pain points, preferred payoff, and priorities without making reps play content detective every time they prep for a call.

A B2B sales enablement system connects messaging to deal stages, not just campaigns, so SDRs stop guessing and start selling with precision and purpose.

Boost buyer engagement by equipping reps with the right resources at the right time

You want reps showing up like pros, not scavengers. So, give them timely resources that feel like magic and land like value in every conversation.

Leading enablement teams put the right things in front of every seller so they can share those materials with buyers exactly when it matters most.

That means moving from a cluttered content jungle to a fully integrated, guided experience that’s not just a random assortment of GTM point solutions.

5 business outcomes you improve with higher sales enablement maturity

“Plenty of obstacles block the path to go-to-market effectiveness,” according to Highspot’s State of Sales Enablement Report 2025. “Inconsistent performance, changing buyer expectations, and technology disruption—it’s a perfect storm that’s leading organisations to adjust their approach.”

One such adjustment? Assessing their sales enablement maturity and taking the requisite steps to improve. By doing so, B2B companies like yours can:

1. Increase win rates and velocity: Help reps execute with greater consistency and focus

Higher maturity changes how sellers show up deal after deal.

Reps arrive prepared with direction, purpose, and a shared playbook that guides decisions amid long B2B buying journeys. That consistency removes wasted motion and replaces scattered efforts with repeatable execution that compounds.

All GTM leaders gain visibility into what supports successful deals and where teams veer off path. Meanwhile, sellers spend fewer deal cycles recalibrating on their own and more time advancing active opportunities with confidence and clarity.

Over time, teams build muscle memory around proven motions, which accelerates outcomes and tightens sales timelines without relying on heroics.

2. Drive seller productivity gains: Reduce time spent searching and customising materials

Sellers’ time remains one of the most expensive resources inside any revenue org.

Higher sales enablement maturity removes distractions that pull reps away from selling motions that matter. Materials stay current, accessible, and easy to adapt without excessive manual effort. Reps begin each day with direction instead of rummaging through folders or rewriting content from scratch.

In turn, sales productivity rises when sellers spend their energy engaging buyers rather than managing assets. As workflows simplify, sellers gain capacity to pursue more opportunities with consistency and focus across their book of business.

3. Improve content utilisation: Ensure SDRs and AEs use what works to move deals forward

Content delivers value when sellers trust it and rely on it daily.

Higher maturity replaces content overload with intentional distribution tied to seller workflows. Both SDRs and AEs gravitate toward materials that earn credibility through repeated success in live selling situations. Sales enablement leaders such as yourself see which pieces earn adoption and which fade quietly.

As time goes on, enterprise content management reflects real selling needs rather than internal assumptions. Utilisation improves as sellers recognise clear relevance between materials and buyer needs throughout complex deal journeys.

4. Accelerate new hire ramp time: Standardise onboarding with role-specific learning paths

Early seller experiences shape long-term performance. Mature enablement creates structured onboarding paths that remove ambiguity in critical early weeks.

New hires gain context, expectations, and practical guidance that mirrors real-world selling environments. Learning builds progressively, reinforcing knowledge through application rather than passive exposure. Managers spend less time correcting fundamentals and more time coaching advanced skills.

Faster ramp for new reps strengthens team morale while protecting sales pipeline coverage in periods of growth or turnover across your selling org.

5. Strengthen forecast and pipeline health: Connect seller actions to real buyer behaviours

Forecast reliability improves when leaders understand how sellers engage buyers throughout the pipeline. Higher enablement maturity links seller activity with B2B buying signals and patterns over time. Leaders spot early indicators of deal health by observing how sellers apply guidance during critical stages.

Pipeline reviews become grounded in observable signals rather than optimistic narratives. Teams gain shared language around what strong opportunities look like in practice. All in all, forecasting evolves into a disciplined practice informed by consistent seller execution and observable buyer participation.

Charting your path to higher sales enablement maturity—with AI by your side

Improving your sales enablement maturity is a never-ending action item.

The top go-to-market strategies and teams treat it as a living practice tied directly to overall business objectives, evolving buyer expectations, and shifting market dynamics. That commitment pulls enablement beyond basic activities and into a discipline that compounds value weekly, monthly, and quarterly.

Momentum comes from intention. The sales enablement teams that pause, reflect, and adjust with focus gain clarity around what deserves attention next.

And when they invest in a single source of truth that’s accessible to everyone in go-to-market, create a single source of truth that helps RevOps, marketing, and sales leaders make smarter decisions together instead of operating in parallel lanes.

That shared understanding turns isolated improvements into coordinated progress.

Bottom line: Tech must play a starring role in your sales enablement journey—and AI is the accelerant that keeps improvement moving at a steady pace.

The difference lies in choosing AI-powered, agentic platforms designed for modern go-to-market teams, not scattered tools with narrow impact. Purpose-built solutions like Highspot connect insight to execution, whereas standalone GTM software struggle to extend value beyond surface-level use cases.

Add on a vendor that acts as a de facto sales performance consultant—bringing guidance, expertise, and services that help teams like yours navigate change with confidence—and you have a dedicated partner that’s invested in your success and helping your org turn ambition into durable progress that lasts.