How to Improve Bookings Per Rep and Why This Metric Matters

By: Phil Stern  |  April 21, 2021

In a prior post, we shared tips for evaluating and improving the effectiveness and efficiency of your sales teams. Now, we want to focus on one critical outcome driven by these improvements: Bookings Per Rep. At Mainsail, we believe Bookings Per Rep is an essential KPI for all sales leaders. Of course, quota attainment is the ultimate outcome by which most sales leaders are measured, but Bookings Per Rep more accurately portrays the overall health of your team and the bookings balance across your sellers.

Bookings Per Rep allows you to measure the impact of your coaching, the effectiveness of your optimization efforts, how well equipped your sellers are with technology, and whether you’re properly scaling the business (not just adding headcount or increasing marketing spend). In other words, Bookings Per Rep can help you understand the cumulative impact of your efforts on the success of your teams.

We recommend focusing on Bookings Per Rep over quota attainment because oftentimes we miss-set quotas, either too high or too low. And—we like having one “north star” metric (instead of many) because of the focus it brings. What’s more, it’s an effective metric because it can be influenced by a number of strategies.

Why measure Bookings Per Rep?

Not only will improving this metric improve your overall sales outcomes, but by focusing on improving Bookings Per Rep, you can spotlight:

  1. The effectiveness of your coaching. If you have an effective coaching plan in place, provide reps with frequent and constructive feedback, and adhere to a sales methodology, you will see a meaningful impact in bookings per rep. And, importantly, you will be developing your people, who will take notice.
  2. The impact of your optimization efforts. Optimizing your funnel, cadences, messaging and alignment with marketing can yield big results. If you are constantly tinkering and testing these areas, you can unlock new potential from your sales teams and increase their effectiveness. These efforts might include lead scoring and prioritization, touch models, outreach cadences, and testing your messaging in email outreach.
  3. The usefulness of your sales technology. The right tech stack is the one that delivers optimal efficiency for your teams. It makes reps faster and more organized, helps them sell with greater intelligence, and enables them to quickly identify what’s working and what’s not. To see if you have the right tech in place, shadow a few team members, and watch them navigate your CRM and other sales systems.
    Pro tip: Measure how long it takes your sellers to wrap up a call. How many screens are they on? How many tabs are open? How many apps do they have to jump in and out of? It is likely that you have room to improve your per-rep efficiency just by tuning your systems.
  4. Your effectiveness at converting your funnel. You need to know your funnel conversion rates for each rep and each stage in the funnel. This can help you uncover who your top rep is—not just who has the best territory. Once you identify this baseline data, work with each rep to improve their performance and increase the yield of the funnel. This exercise is good for the reps, good for customer acquisition costs, and good for your business.

Practical tips for increasing Bookings Per Rep

Part I: Know your baseline measurements and track the right metrics
There are many metrics you can track to gauge the effectiveness of each rep. Here are a few that I always track because I find they offer the best comparison points. For each, you should set up a related coaching strategy.

  1. Conversion rate by rep: Many teams look at this solely as a rolled-up, full-team metric or even delegate it to marketing. We recommend that all teams track conversion rates by individual rep for all steps in the funnel.
  2. Discounting by rep: Tracking (and reducing) this metric tells you two things about your reps: 1) Who is using discounts as a crutch to close instead of winning with a strong sales process and 2) Who isn’t maximizing the value of each deal.
  3. Average Revenue Per User (ARPU) or Annual Contract Value (ACV) by rep: Yes, these metrics include discount rate per rep, but they also analyze who is selling your premium tiers, adding on services, cross-selling other products, etc.
  4. Multi-product attach rate: This is included in ARPU but it’s worth breaking out. Understand who is winning with transactional, quick-hit sales and who is uncovering needs and working with clients to find solutions. Reps who run a thorough process and take the time to understand their prospects often have the strongest cross-sell and upsell performance.
  5. Retention by rep: Who is selling the highest quality deals? Who is best at qualifying prospects in or out of the funnel? Establishing urgency? Showing value before the sale closes? Supporting new clients through implementation?
  6. Referrals by rep: This not only speaks to the relationship your reps are establishing with their prospects during the sales process—it also shows their desire to build their business to help the company grow. Tracking referrals by rep is as simple as adding the right lead source into your CRM and laying out the process your reps should follow when they source a referral opportunity.

Part II: Prioritize conversion rates
This is the biggest needle-mover to get more customers in the door. More customers will help your business grow and help keep your reps feeling successful while you continue to focus on improvements.

  1. Train on your Ideal Customer Profile. In addition to sharing personas and other internal materials with your teams, get them in front of your ideal customers. Even in a remote environment, holding customer spotlights over Zoom will help your team develop empathy for, and understanding of, your customer and how they derive value from your product.
  2. Train sales skills. Bring on a sales methodology; hold regular 1:1s; score calls; shadow; and encourage all team members to share best practices with peers.
  3. Ensure you have the right tools. Assess your sales technology. Is it helping your reps be more efficient or is it slowing them down? Investing in tech can get you more productivity per rep and cleaner data. Win-win!
  4. Review your strategy. Do you have the right sellers focused on the right deals? Equitable territories? Smart lead routing? Clear priorities? In other words, are you enabling your reps to be as successful as possible or are you inadvertently distracting them from their core objectives?

Part III: Increase your ACV or ARPU
In addition to training on sales skills, help your reps increase the value of the deals they’re selling.

  1. Reduce or remove discounting and special offers. Reps can get comfortable offering discounts to help close deals. If you reduce/remove discounting and lead your team with discipline, you’ll see this evaporate. Reps will close deals for the right reasons, and your business will be better for it.
  2. Enable cross-sell and upsell opportunities. Partner with your product development leader to identify, build and release ancillary products that customers will benefit from. Or, review your pricing and packaging.

Part IV: Evaluate and adjust your headcount model

  1. Review your headcount model every quarter. If you don’t have one, build one. By reviewing the model quarterly, you can spot issues. And, you can challenge yourself to improve bookings-per-rep as opposed to simply adding headcount.
  2. Right-size your team. Sometimes adding reps to help grow the business is the right answer, but oftentimes it’s not. And reps who are hitting their quota—at least more often than they’re missing it—will have higher morale and more motivation. If you’ve hired well, you’ll be more successful with a highly motivated, smaller team, than a newly hired larger team that is struggling to hit its numbers.

Part V: Tune your comp plans

  1. Ask your reps. We know they’ll say they want more money. But by simply giving them a voice, you will head-off potential issues. And if you plan to make changes to your comp plans, involve them in the solution.
  2. Validate their comments with data. Partner with your finance leadership or your CEO to look at specific comp plan scenarios. Share these concepts back to your sellers.
  3. Use your data and rep insights to answer:
    1. Am I doing the right thing for our sellers and leaders?
    2. Am I promoting responsible unit economics for the business?
    3. Will this comp plan drive the right results?
  4. Commit to regular reviews and revisions. We recommend twice yearly comp reviews and potential adjustments to the plan.

Part VI: Review territories or books of business
Not every rep will have the same skill level or drive to succeed. But all reps should at least feel they have a fair shot at hitting their quota.

  1. Do the analysis. Are territories evenly built? Are leads appropriately routed?
  2. Commit to change. Commit to an openness to change routing policies or territories at least quarterly.
  3. Communicate often. Share details with your team members. Instead of letting your sellers stew over what they perceive to be unfairness, be transparent with your data and how and why territories or lead-routing is set up.

By focusing on Bookings Per Rep as your indicator of the effectiveness and efficiency of your sales team, you put the performance of your people front-and-center and incorporate a large and diverse set of metrics into your month-over-month view of your team. Remember, this is a multi-quarter and multi-year journey, not a project with a start and end date.

Phil is a Operating Principal at Mainsail Partners. He leads the firm’s Center of Excellence for Sales and is responsible for helping Mainsail’s portfolio companies optimize their growth strategies and deploy sales practices.
More by Phil Stern
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