Strong Frontline Management: An Essential Ingredient in Startup Sales Success

October 3, 2019

Sara Howshar

In startups and other fast-growing companies, sales organizations are so busy chasing customers and revenue that they fail to focus enough time and attention on building a strong foundation that will support their long-term success. That foundation includes technology, processes and skills.

Failing to build a frontline management foundation early can create challenges that will be all too evident to investors. #

“Sales teams need process and discipline as they grow,” says Don Drury, Founder and Principal of Drury Advisors, a Boston area-based consultancy that helps small and midsize B2B organizations improve the performance and productivity of their sales and marketing teams. “And there are a lot of implications for businesses if they don’t have their ‘machine’ on the front end really tuned up.”

Drury explains that building strong frontline management and developing consistent processes for the sales team, particularly around coaching, can positively impact everything from forecast accuracy to pipeline quality to overall performance.

Joe Caprio,’s Vice President of Sales, interviewed Drury for a recent episode of The B2B Sales Show podcast. They explored some of the benefits that startups (and all companies, really) can realize by strengthening their frontline management in sales.

In case you weren’t able to tune in, here are 3 things they discussed:

Takeaway #1: Strong frontline management can help protect the bottom line. #

Sales team churn is just one of the “very expensive problems” Drury says companies can struggle with when they have weak frontline management. Frontline managers often fail to make coaching a priority because they are new to management. Or, they don’t know how to coach effectively because they weren’t taught best practices. So, their reps don’t get the guidance they need to succeed — whether they’re new and need a firm hand as they ramp, or they’re more experienced and craving feedback that will help them develop their A-game.

Another very expensive problem for a growing business — which can result from the combination of weak frontline management and poor coaching practices — is margin erosion, according to Drury.

When it occurs, some questions sales leaders should ask so they can get to the root of the problem include: “Is discounting going on? Are frontline managers not able to get reps to hold their position on value during negotiations? And what is that doing to the selling price and the length of the sales cycle?”

Takeaway #2: More structure in one-on-ones and team meetings can bring more structure to the sales organization overall. #

One frontline manager alone cannot bring more consistency and predictability to sales practices and processes in the sales organization.

Instead, everyone from the top down on the sales team needs to “line up with the structure,” Drury says.

There are two places to add more structure, and define/measure what sales success looks like for the startup’s sales organization. And those are weekly one-on-ones and team meetings. #

Infusing more structure — and meaningful coaching — into these meetings helps learning and best-practice sharing to cascade down through, and across, the entire sales organization.

In one-on-ones, managers can give actionable feedback to their reps, and reps can raise issues and request the support they need to perform at their best.

To ensure these meetings are a two-way discussion, Drury suggests giving reps a “guide” (Read: A clear agenda) in advance that will allow them to come to the meeting prepared to talk specifics. And managers should be ready to coach in these meetings — for example, by asking open-ended questions such as, “Have you tried this … ?” when a rep reports they are facing a problem.

Team meetings are an ideal opportunity to “share topics other than just a pipeline review,” Drury says.

Consider this flow for your next sales team meeting:

  1. Managers should consider inviting reps to talk about a deal they have in the pipeline that they expect to close soon, or that they may be struggling to move forward.
  2. Team members in the meeting can share their thoughts on how best to seal the deal and/or overcome the obstacle.
  3. Managers can also use these meetings to highlight what the team is doing well collectively, and invite discussion about shared challenges.

“We are a culture that supports each other. Management doesn’t just tell us what to do.” This is what Drury says reps should leave team meetings with. #

A few team meeting tips from Drury:

  • Managers hold team meetings once or twice a month, “at a minimum.”
  • Don’t make team meetings a rundown of all the latest company news.
    Share that type of information in other communication channels, like an email newsletter.
  • If latest company news must be shared, limit its space in the agenda to about five minutes at the top of the meeting.
    If it’s groundbreaking news, absolutely (and briefly) include it. Then pivot to best-practice sharing, conducting role-plays, and film reviews.

Takeaway #3: It’s never been easier for sales leaders to track the effectiveness of their frontline management — and drive improvement.

How can sales leaders know whether their frontline managers are doing the right things to create consistent, repeatable, and predictable sales processes and practices? By using sales enablement tools, such as the conversation intelligence platform, which provide insight into everyday activities and overall performance and effectiveness.

According to Drury, sales leaders should be actively seeking insights and saying things like, “I want to know what’s happening in coaching calls. Show me metrics. I want to look at calendars.”

A simple survey can also go a long way toward understanding whether managers and reps are on the same page with coaching quality.

Drury says coaching is an area that senior leadership needs to “inspect” regularly, and they will often discover through the survey process that there is a disconnect between what managers believe they are providing to reps, and what reps feel they are getting from the experience.

Identifying the disconnect between perceived and actual coaching effectiveness is critical to driving change that will strengthen frontline management, and help the whole sales team perform optimally. #

For more insights from strategic sales and marketing expert Don Drury of Drury Advisors, and additional details on how sales leaders can put the advice above into action, listen to the latest episode of The B2B Sales Show, “A Quest for Consistency: Why You Need to Focus on Frontline Management,” available here.

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