How One Sales Enablement Programme Increased Sales Rep Attainment at HubSpot by 31%

I’m privileged to have the role I do at HubSpot. Leading sales enablement programmes for over 100 sales professionals is challenging, rewarding and lots of fun. No two days are the same and at any given moment I play the role of coach, advocate and advisor.

The way I see it, my role primarily is to partner with the sales organisation, so sales reps are successful, which enables sales reps and by extension, HubSpot to grow. The goal I’m measured by and keep the closest eye on is whether our sales organisation hits quota each month. Fortunately, I have a number of plays and tactics at my disposal which can positively impact that number - broadly, they are sales training, deal support, sales content and sales productivity.

I want to use this post to tell you about the sales enablement programme I led at HubSpot, which consisted of sales training and deal support, and how it increased sales rep quota attainment by 31%. We saw a big improvement and I’m pleased to say the results had a material impact on annual recurring revenue (ARR), quota attainment and growth. This post covers the approach, format, positioning and results achieved with the programme, and ideas for you to apply at your own software as a service (SaaS) company.

Before we dig into the programme, I think it’s helpful to share some more detail about my role at HubSpot, the goals I focus on and how this fits with the programme. As I’ve mentioned, the overarching goal I try to hit each month is to ensure HubSpot’s sales organisation hits its quota attainment goal. This is a goal I share with HubSpot’s sales leadership - indeed, I’m a firm believer that shared goals are the one true way to drive alignment between teams.

In addition to hitting quota, I also carry a revenue goal. Having a revenue goal is uncommon for a sales enablement function (I make a point of speaking with sales enablement colleagues each quarter to understand their plays, goals and strategies and many of them are a mixture of surprised, shocked and confused by this goal), but to me it makes perfect sense. If sales enablement professionals want to be tasked with influencing revenue, then it stands to reason they must be comfortable carrying a revenue goal. And if you’re interested, we also track and have goals against demo to close rate, and net promoter score (NPS), which provides a snapshot of how sales enablement is supporting sales reps.

How One Sales Enablement Programme Increased Sales Rep Attainment at HubSpot by 31%

Programme overview
Unfortunately, there’s some numbers from the programme that I can’t reveal. However, what I can say is, 78% of sales reps that participated in the programme improved, and average quota attainment of the group increased by 31%. These two numbers are important and show that the programme worked, but what’s more valuable and what I can share is how we achieved these results.

In terms of programme design, we listened to what sales reps were telling us they needed, looked at performance data, and then went and built a programme based on this information. The approach we took may sound simple, but in ruth, it’s rarely done. The sessions were coaching and whiteboard-led, with an emphasis on providing deal support to sales reps. Deal support was a big part of the programme for good reason - HubSpot data shows when sales reps leverage deal support, they close at a 20% higher rate than deals without it.

Why we ran the programme
As an individual contributor (IC) I’m constantly thinking about where I can invest my time to support HubSpot’s sales reps and have the biggest, rather than incremental impact. At the beginning of 2017 we made a bunch of significant changes - these impacted everything from our sales motion to compensation structure to product line. In short, we made some big, transformational bets and made them quickly.

As Q1 drew to a close, our topline numbers were strong, however there were some sales reps not hitting quota. Having studied the quarterly sales figures I identified a cohort of sales reps averaging less than 95% quota attainment in Q1. This got me thinking about how I could best enable them to get to 100%+ quota attainment as quickly as possible. The business rationale for supporting this cohort was strong - as a company HubSpot has aggressive growth plans and to ensure we realise them, we need sales reps to be hitting quota.

At this point it’s worth sharing my sales enablement philosophy. I believe that if the sales enablement function is to succeed and become a genuine partner, rather than servant of the sales organisation it must share some of the same goals. For instance, if the goal of the sales organisation is to hit 110% quota attainment, then sales enablement should also have that goal. If the sales organisation is succeeding then sales enablement should feel good, and if it’s failing, then it should also feel the same pain. It doesn’t need to be anymore complicated than that.

A/B testing, cohorts and coaching
As marketers we’re well acquainted with the value of A/B testing and cohort analysis, so I wanted to apply some of this thinking to sales enablement.

Specifically, I was keen to see if running a programme for a cohort of sales reps would improve quota attainment. Too often we deliver one-size-fits-all training, which is not tailored to the needs of sales reps. Secondly, sales reps tell us they prefer coaching and whiteboarding sessions, as opposed to lecture based trainings that rely on PowerPoint or Google Slides.

Here’s something that is uncommon within the world of sales enablement and learning and development (L&D). We ran an A/B test during the programme. One group of sales reps were invited to join the sales enablement programme and another group were not. This may seem unfair, hard and controversial, but it would provide us with valuable data to evaluate and benchmark the programme.

We knew that we had to get the structure of the programme right, so I consulted with sales managers and sales reps, and eight weeks felt like the right duration for the programme to be able to have a measurable impact. On the topic of learning, I think being purposeful about your own personal development and carving out time each week to learn is the best thing sales reps can do. It sounds like a simple thing to do, but few sales reps actually make learning part of their weekly routine. Oftentimes sales reps find themselves so focussed on short-term results, that they can’t look beyond hitting quota.

Back to the programme. I interviewed several sales reps and scoured previous training feedback to gain a deeper insight into what sales reps felt was valuable about training. The feedback was not surprising - sales reps preferred whiteboard-led sessions, rather than training dominated by slides, smaller class sizes were more effective and training was more valuable when delivered by a subject matter expert, instead of a generalist trainer. Sales reps also liked training to be agile and heavily tailored to their needs, rather than overly structured. In short, they preferred coaching to lectures. Much of this may sound obvious, and while feedback was being gathered, it was not being acted upon.

The final structure we decided on for the training programme was seven, 45 minute training sessions held over eight weeks. I also committed to meeting with each sales rep individually biweekly for 15 minutes to provide deal support in the form of deal strategy, setting up customer reference calls or providing competitive intelligence. The purpose of the deal support meetings was to identify opportunities where I could support sales reps to close deals.

Guiding principles
The programme was designed to be agile, scrappy and different. Based on discussions with sales reps we created a set of principles to codify what the programme would be about. This would provide clarity for both participants and subject matter experts, who delivered the training.

I want to acknowledge that the programme was heavily tailored to the needs of the group, so scaling and replicating the programme exactly is a challenge. But I’m okay with that - I’d rather run a programme that is effective and tailored to the needs of sales reps, but lacks scalability, versus one that scales well, but is poorly suited to the needs of the sales reps. In truth, I was keen to test if this new approach would work -  we could tackle scale afterwards.

More generally, when you’re innovating and attempting something new it helps to create principles that clearly show what something is - and of equal importance, what it isn’t. This reduces ambiguity and grey areas, and helps show to everyone how we’re trying to do something original and improve. I shared these principles with the subject matter experts two weeks ahead of their session, so they understood what we wanted to achieve.


Having worked with sales reps across a wide range of industries for over a decade now, it’s clear there’s only two types of sales rep. The one that is hitting quota each month and the one that is not. Confidence, momentum and trust are tough to create and easy to damage, so for that reason we wanted to be extremely emphatetic about how we communicated and positioned the programme. This wasn’t a pre-performance improvement plan (PIP) move - it was quite the opposite. The sales enablement programme represented a big investment, but we believed that with additional support this cohort of sales reps would be able to hit 100% of quota attainment.

Programme schedule
The very first session was used to introduce the programme to the sales reps and to understand their needs. In conjunction with the sales managers and leveraging performance data, a menu of options was created. The sales reps were encouraged to consider what areas they needed to develop - and then they had the opportunity to select the most valuable sessions, as well as add sessions to the list. As a group we then whittled down the list until we had a programme that would meet the sales reps’ needs.

During the initial session we also asked sales reps for “an all or nothing” commitment. They could come to all of the sessions or none at all. I’m convinced that by getting sales reps to co-create and then commit to the programme they felt bought into it and what we wanted to achieve.

In case you’re interested, the sessions our sales reps decided on were a mix of tactical advice for specific deal stages and softer sales skills. Below is the list of sessions in the order they were delivered:

  1. Programme introduction and need’s analysis

  2. Uncovering a prospect’s true business need with active listening

  3. Delivering a high impact connect call and tie downs

  4. Bringing your demo to life with storytelling

  5. How to deliver a winning demo

  6. Negotiation and building tension to drive a deal forward

  7. Time management

Sessions were designed to be practical and the goal was that sales reps would leave with actionable steps they could implement immediately. To ensure sales reps were completely focussed on each session we asked them to keep their laptops off and I was notetaker. This kept sale reps engaged with the discussion, and they all received the same notes on the session later that day. We also surveyed sales reps immediately after each session to understand if the content and subject matter experts met their needs.

The programme was ran over an eight week period in Q2 and achieved the following results:


In addition, the average NPS for the subject matter experts was 67 and for each session it was 63. I know measuring the impact of training is difficult - so as I’ve mentioned, we ran an A/B test. Interestingly, the group of sales reps not invited to the programme on average increased quota attainment by 9%.

The was no secret hack, tactic or ingredient. To put it simply, we spoke with sales reps to understand what they wanted from training and then delivered a programme based on what sales reps told us, plus what data and sales managers showed they needed. Most importantly, sales reps engaged with the programme - I believe the way we positioned and communicated the programme was essential, but ultimately, the sales reps themselves, must take the credit.

Taking a step back, I’m not surprised by the improvement. Being purposeful about learning and setting aside time each week to learn is how you improve. We see a lot of potential in the programme - not just the increase in quota attainment, but the high NPS, so we’re doubling down and rolling it out globally at HubSpot. I'm excited to see how we can help sales reps improve in Q3, 2017 and beyond.