Categories Articles, SaaS

There’s a persistent belief in sales that analytics only benefits management.

If you say “data-driven sales” to most reps, they immediately think of the frustrating process of entering data into Salesforce. Pipeline reviews, forecast meetings, and quarterly business reviews all seem like a waste of time — valuable time — that could be spent doing something mission-critical, like selling.

I know, because I was one of those sales reps. I couldn’t understand why it mattered to talk about every deal I lost, and how many days it sat in my pipeline. I felt like the most important part of my job was to move forward and focus on today’s open opportunities. I resisted the data deep dives I was subjected to, because I didn’t see the benefit to my sales results.

But now, I know better. To the reps who say they can’t use analytics to improve their results, I would push back. By using my historical data to help drive my existing pipeline, I improved my win rate from 8% to 11% and closed my biggest quarter ever.

I closed my biggest quarter ever.”

If you’re interested in seeing results like this, it’s not magic — it’s the blend of art and science that we hear about so often. All I had to do was own my sales pipeline — analyze the data, find improvements, and focus on the opportunities that are most likely to turn into Closed-Won deals. Data doesn’t lie, and neither do the results.

The Power of a Data-Driven Pipeline

Last July, my sales director, Ben Theriault, sat me down for an in-depth 1:1 to dig into my personal sales performance analytics. Rather than discuss what he thought were the areas I should improve, he asked me to pull up a few reports on my trending performance, activity, conversion rates, deal velocity, and pipeline flows. We looked at this information in light of my own past, as well as relative to others on my sales team.

He highlighted 3 things as we strategized to dominate second half of the year. Using the data, Ben pointed out specifics:

1. I converted a lower percentage of opportunities from Discovery to Evaluation (19% vs. 27% average for our team).

2. It took me longer in the Discovery stage, and the difference was massive for opportunities I’d eventually lose (63 days vs. 40 days for the team).

3. I consistently had 35 to 40 opportunities in my pipeline, while the rest of my team had between 15 and 25.

These numbers all differed quite a bit from the rest of my team — who sell the same product, to the same people, with the same internal resources. At first, this didn’t seem like a big deal to me because I had a similar overall win rate. But I soon realized that all of this information was an opportunity to drive more wins.

Honing in on My Weak Spots

Instead of resisting what the data told me, I decided to embrace it. The data said that I had a huge opportunity to improve my win rate with a focused effort. No matter how you sliced it, I was worse than my peers at one specific part of our sales process: Discovery. My director began to focus our weekly conversations on opportunities in this stage, and how I could improve my results. While giving more leeway with other opportunities in other stages, he questioned me hard on these opportunities:

  • Why now?
  • Are we working with the right people?
  • What do we need to do to move each into an active evaluation process (our Stage 3)?
  • Is there an actual priority within their organization, or are they doing personal research?
  • What are we trying to help the business achieve?

My weekly meeting with my director turned into highly focused pipeline reviews of all of my Stage 2 opportunities. He asked more questions and gave me more pushback on my answers. We talked about who were real candidates for our product, and who were just tire kickers. Through this process, I learned I had been blind to certain signals that were staring me in the face. Ultimately, curiosity and interest don’t sign a contract and check.

Throughout this data-driven process, I learned a number of valuable lessons, including:

1. Know my weak spots, and get the right help at the right time.

There are a lot of reasons it takes some sales reps longer in certain stages of the sales process.  When I think about my performance vs. others on my team though, there were 2 things contributing: 1) difficulty getting folks into our evaluation, and 2) holding on to bad deals. The best way I could think to look at this was by meeting with other reps, and comparing notes on different opportunities, in my pipeline and theirs. Over lunches and beers with folks on my team I picked up some specific tactics others had in this part of our sales process, and used it to drive improvements in my execution.

2. Figure out where I can accelerate deals by learning from peers.

It also turned out that I had a higher bar before I’d “give up” or let go of an opportunity. Said a different way, I was chasing opps in the Discovery stage who were not great prospects, and trying to create something out of nothing. Letting go of futile pursuits earlier was a big personal win — I reduced the number of days I was chasing a bad deal in the discovery stage from 63 to 50 days. I could now refocus my time on higher-value efforts.

3. Time really is money.

The other piece of the puzzle was the sheer number of sales engagements I was running. It didn’t take a conversation with my manager to realize that I was having a hard time fully focusing on 40 sales engagements. The truth is, one quarter of those were as cold as ice, and I was waiting on a miracle to revive them.

“I over-invested in the opportunities I knew I could win.”

I imagine for my Sales Director it was like pulling teeth — trying to get me to close out opportunities with no traction that I believed I could revive. At one point, I had a two week period where my open pipeline had plunged from 39 opportunities to 19 in just 2 weeks. I was really worried and at the time, it felt like the wrong move. I thought that by narrowing my pipeline so significantly, I wouldn’t be able to hit my goals.

In retrospect, this was the turning point. Eliminating bad opportunities allowed me to over-invest in the opportunities I knew I could win — the opportunities that “looked like” the deals I win historically. (By the way, if you’re looking to figure out how many opportunities you need, and how they should be distributed through your pipeline, I recommend this article and downloadable excel model for folks who don’t have access to a sales performance analytics platform like InsightSquared).

In line with letting go of Stage 2 opportunities that the data told me didn’t look and feel like winners, I also started letting go of opportunities in other parts of the sales process. I realized these cold opps were taking my time and resources away from the deals I was more likely to win, and wasting my time.

The Results

With this renewed focus, I was able to narrow my pipeline and increase my win rate. In fact, I improved my Stage 2 to Stage 3 conversion rate from 19% to 38%, and my overall win rate from Conversation to Closed-Won jumped from 8% to 11%. Said differently, I am now winning 37% MORE deals.

I won more deals simply because I concentrated on the winnable sales engagements. I stopped spreading myself so thin, and over-invested to win the deals I knew I should win.  

By trusting the data and altering my behavior according to the numbers, I blew my quota out of the water. My takeaway? Doing a deep dive on my own historical performance enabled me to isolate the areas where coaching and extra attention could have the most immediate impact on my overall performance. Then I made the changes that were necessary to succeed.

It’s true: sales reps don’t like to admit when they need help. In my case, the data was clear. With my manager on my side and the data optimizing my efforts, I executed a strategy that simply worked. Sales is hard — why fly blind?

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