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The Future of Sales Enablement

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The Future of Sales Enablement

Sales enablement is undergoing a seismic shift. The changing macroeconomic landscape, advances in AI, and evolving buyer behaviors are reshaping how organizations empower their sales teams. This week we’re unpacked these trends and actionable strategies for navigating the changes – let’s get into it.

Defining sales enablement in 2025

Sales enablement remains a somewhat ambiguous concept. This is due to the fact that enablement spans a vast spectrum — from content and training to strategic adoption of tools like AI.

If you ask three leaders for their definition of sales enablement, you’ll likely get three different answers. For example, three go-to-market leaders define it as:

“Proper sales enablement means I don’t have to be around as much. It’s about empowering the team to do their job faster and more efficiently with minimal oversight.”

– Ryan Ball (VP of Sales at Birdeye)

“Sales enablement is the holistic ownership of the knowledge, skills, and abilities sellers need to succeed.”

– Lisa Kelly (Head of Sales Operations at BambooHR)

“It’s about giving reps the best chance to win at scale.”

– Jacob Fleisher (Head of Sales at Attention)

Overall, a broad shared perspective is that sales enablement is about equipping sales reps with the tools, knowledge, and skills to succeed at scale.

Why the enablement landscape is shifting

Many factors are driving change but there are two that are doing so seismically.

1. Buyers are smarter and more self-sufficient

Modern buyers enter the sales process later than ever, often after completing their own research. This requires a shift from “educating” prospects to disrupting preconceptions and creating value.

“The world has changed dramatically in the last few years. It used to be easier to guide buyers through the process, but now they come in later and much better informed.” – Ryan Ball (VP of Sales at Birdeye)

2. AI is redefining enablement

AI isn’t just a tool; it’s an accelerator. It’s about giving sellers the feedback and insights they need in real-time to improve without waiting on managers to intervene.

At BambooHR, overall AI adoption increased sales attainment by 21% among super-users compared to their peers.

Tips to implement AI:

  1. Start with behavior change: Encourage teams to adopt AI tools like ChatGPT in daily tasks, building familiarity and confidence.

  2. Governance matters: Form committees to evaluate AI tools and create clear guidelines for their use.

  3. Measure impact: Track adoption and its effect on performance metrics like quota attainment and velocity.

The new priorities for sales enablement

Many priorities remain the same, with alignment and execution still being focus. What’s different is how quickly you need to adapt your approach to keep up with market changes.

Two key areas around that are surfacing:

1. Balancing GTM updates and skill development

There’s a critical distinction between go-to-market updates — like new products or workflows — and skill development, which requires hands-on learning.

GTM updates are informational, while skill development requires reps to be in the right psychological state for active learning.

Having separate forums helps to strike a balance. For example, deliver GTM updates through emails or asynchronous videos, while conducting skill development in workshops or coaching sessions.

2. Leveraging AI for targeted coaching

AI offers the ability to scale coaching in a way that manual efforts never could. But to be effective, AI tools need to align aligned with business goals and seamlessly integrated into workflows.

For example, BambooHR implemented Attention for AI-driven coaching, which has enabled their team to optimize workflows, analyze calls, and create tailored training programs.

“AI allows managers to identify specific gaps in rep performance, like talking about pain points, without combing through hours of calls.” – Lisa Kelly (Head of Sales Operations at BambooHR)

Adapting to the new buyer-seller dynamic

The way buyers purchase has changed. Today’s buyers have already done research on their end and demand a deeper understanding of their business needs.

Tips to adapt:

  1. Shift conversations from latent to active needs:

    • Understand the prospect’s organizational goals before pitching a solution.

“Help sellers recognize whether they’re the ‘column filler’ or truly solving a problem.” – Lisa Kelly (Head of Sales Operations at BambooHR)

  1. Focus on the three “whys”:

    • Why now?

    • Why anything?

    • Why us?

“These questions frame conversations in a way that digs deeper into customer priorities.” – Jacob Fleisher (Head of Sales at Attention)

Metrics to measure enablement effectiveness

Sales enablement is only as effective as the results it produces. Measuring impact is critical to proving its value and continuously improving strategies.

Tips on metrics:

  • Time to Productivity: Measure how quickly new hires ramp up to full productivity.

  • Dollar Per Day Spent Selling: Evaluate reps’ velocity by dividing ACV by the time opportunities are open.

  • Adoption Rates: Track adoption of enablement tools and strategies through usage and performance data.

Sales enablement isn’t just a department, it’s a mindset. It’s where the rubber meets the road, turning strategies into actions that empower sellers to drive results. This mindset is necessary for the changing landscape as we move towards 2025.

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This newsletter was entirely written and edited by Sophie Buonassisi and Scott Barker (not AI!).
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