And they're easy as pie. 

When done right, a sales enablement strategy creates powerhouse sales and marketing teams: there's great synergy, everyone is empowered and enthusiastic, there is vision and goal clarity… It almost feels like choreography. Just add music. 

a coupla dancing

As a sales veteran, and now as a solopreneur, I've headed my own share of sales enablement strategies and interventions. Most worked, and the rest I learned from. 😀

I've also had amazing mentors and colleagues, and now, in my startup communities, I'm part of some great conversations. 

In this post, I'm distilling all this collective wisdom into these best practices. Since most of my experience is in the SaaS startup space, that's where my perspective comes from. Having said that, this list is fungible - what SaaS startups go through, other businesses do too. 

Involve your people 

Involve your sales and marketing users in shaping enablement strategy. Not only will it improve ownership, but also adherence. By involving the users most affected by these changes, you're giving them a chance to contribute to fixing their own problems, and more often than not, they already know what's wrong and what needs doing… it's just that they haven't had a platform to express it. This is their daily bread, after all. 

Also, wherever possible, run trials and pilots. Sometimes ideas that seem great on paper just don't translate because we've failed to consider some critical factor. It happens to the most experienced of us. Each organization, each team, and each team's culture is unique, and even 'proven' solutions and strategies have a way of failing from time to time. 

Automate whatever you can, whenever you can. 

This is the age of ChatGPT and award-winning AI art. Challenge your assumptions on what's possible when it comes to automation. I recently reviewed a number of automation - everything from Email Tracking to Training and LMS tools, to Sales Intelligence, to my favorite topic: Demo Automation

You'd be surprised at how much of the work our teams do is repetitive. And nothing makes a dull sales rep like repetitive tasks. Sales is hard enough. It doesn't need to also involve the drudgery of endless data entry, writing a million emails and making a gazillion custom demos. There are tools for all of that now. Wherever possible, take away grunt work, and watch your salespeople plough all that time and effort back into nurturing your clients and prospects. 

Record, replay, feedback. 

One of the best ways that sales reps improve their performance is by watching themselves at work and performing their own critique. The best aha moments come from within, right? :) There are a number of tools that run the gamut from basic call-recording software to AI-powered conversational intelligence. Start with what you can afford, and build as you grow. 

Create structured opportunities for feedback - be it buddy reviews of one another's demos, sales engineer-sales rep groupings that get together from time to time, or cross-functional mixers where people get to break down what went right and what went wrong in a case study. The more we understand the downstream effect of our actions, the more we care. 

Get marketing and sales to work together on content 

Yep, sales and marketing synergy. For two teams that have so much in common, marketing and sales teams can often work at loggerheads. When they don't work well together, your ability to qualify and convert leads suffers, as does the quality of the content you're generating. However, when you have mechanisms to bring these teams together effectively, you end up with stellar results. 

For starters, teams create much more accurate buyer personas. They're able to give feedback to each other on which messages are resonating best: marketing gets feedback on how successful their content really is, and sales are able to refine their messaging based on marketing's insights. You end up with much stronger sales and marketing materials, and dare I say, alignment on goals and vision! 

Create content libraries (and value-added content) 

In the era of value selling, sales content needs to go beyond the standard sales collateral, demos, case studies and whitepapers. Your intention here is to deliver value and to do so, you need a bank of data that your sales reps can share with the prospects they are nurturing. Access to marketing and domain intelligence for industries you're targeting goes a long way when sales reps are trying to identify pain points, and create meaningful value-added conversations around these. 

Of course, you could have the best sales collateral and market intelligence, and be let down by how hard it is to find this data. Invest in a good content management solution, yes; but bring your sales team along for the ride. Unless the solution works for the end user, it doesn't work. Better yet, let your sales reps be involved in the purchase decision, demos, and the whole shebang. A solution they've had that much input in will see good use. 

Creating a culture of curiosity (not blame) 

A good sales enablement strategy is one that gets reviewed regularly. Using our sales metrics as a guide, it's essential to delve into the root causes of our losses. Why are we seeing an increase in drop-offs after discovery? Why are we seeing a lower response rate on email? And so on. How we ask these questions is probably more important than the questions themselves. 

Sales organizations are competitive, hard-driving spaces. It's very easy to put people on the defensive, especially if they come from organizations that had really punitive cultures. This is why it is important to approach these questions from a space of curiosity. This is where the sales leader sets the tone. 

For me, what has worked best is to meet the teams or individuals who are struggling most, and express my curiosity. When they know this is not coming from a place of blame and shame, they usually open up and tell me what the real problems are. I also make it a point to never go into these questions during my weekly/monthly reviews - it's not the forum for it. 

The more you practice curiosity, the more your teams learn to expect it, and the easier it gets to find your way to the root causes of problems and take necessary action. 


We're all learning: there isn't a sales leader alive today who claims to know everything there is to know about sales enablement. In the same vein, there is no perfect sales enablement strategy. We're trying to create strategies that work well and accomplish the goals we set out to achieve. And then we get up the next day and tweak them some more, and more, and more. 

My recommendation is to not do it alone. Build your tribe of trusted confidants and advisors, create open communication channels that encourage your people to approach you with problems and solutions, and keep your eyes and ears open! We'll make mistakes (even some avoidable ones), but we'll get there. 

At heart, we're still scrappy sales reps, and our biggest superpower is still our tenacity. We've got this.