Outside sales reps deal with challenges on the road that most office-bound reps rarely think about — what to wear, where to go, how to get there, and when to report back add multiple layers of complexity to sales.

The challenges don’t stop there, however. Many reps struggle to get quality sales information into their CRM during the day (and the last thing anyone wants to do is spend the evening in Salesforce). What’s more, they work apart from the rest of the sales team and miss out on the same progress reports and motivators their peers get in the office.

It’s also difficult for sales managers who are trying to give them guidance from afar.

“[One of the main challenges] is that I don't see their work every day. It's an obvious challenge but also a hard one. It just means that it's not as simple as just looking over their shoulders and getting to the lowest level of detail immediately.” 

—Jack Momeyer, Director of Sales, DoorDash

As head of outside sales for DoorDash since 2017, Jack Momeyer knows firsthand the challenges that come with managing on-the-road sales reps. Jack oversees six senior sales managers who work with 7-14 sales reps each. Those reps work primarily in the field, signing on restaurants for the DoorDash service.

To help sales managers in similar situations, we brainstormed the main challenges facing outside sales teams and chatted with Jack to get his insight on how DoorDash overcomes them.

Challenge 1: The Right Information Isn’t Getting into Salesforce Quickly Enough (Or At All)

“We are in the field a lot, and our reps aren't always logging calls from the field. They might write stuff down on paper and then do it that night. They might not do it at all.”

The reality is that outside sales reps spend most of their workday on the road doing sales calls. They have little opportunity to pause long enough to unpack everything they learned at their last meeting into the CRM.

This means they often spend their evenings typing everything into Salesforce when they’d be better off relaxing after a long day on the road. This isn’t great for your sales reps’ quality of life — nor is it good for the quality and timeliness of the information available to you and the rest of your team.

Solution: Give Reps the Ability to Update Quickly, on the Road, When it Matters

One way to overcome this challenge is to enable your sales reps to quickly and easily update the CRM on the road. This gives outside reps the option to quickly complete tasks, depending on the amount of time available to them at that moment.

imageYou can do this using automated alerts to prompt your reps to update snippets of valuable information from their devices. For example, a rep can spend a six-minute Uber ride between meetings updating a sales forecast from their smartphone. Arrive early? Make the most of that 20 minutes sitting in the parking lot by updating your sales process fields.

The alerts should be contextual, prompting reps to complete important tasks when they matter most and make the most sense. For example, you could set up an automated alert reminding a rep to fill out opportunity information immediately after a sales conversation.

Context is important as it helps reinforce sales behaviors and prompts reps to cross off items on their to-do list throughout the day.

These little efforts reduce the burden on reps to document everything (and do so accurately) at the end of the day. They also ensure you and the rest of your sales team have access to the most recent deal information.

This use case is the reason DoorDash started looking for a tool to help their outside reps update Salesforce from the field.

“All in all we [thought we could] save some time, get better inputs, understand our business better, and forecast better if we had a tool in place that is a little bit more seamless.”

In the end, they decided to use Troops alerts to empower their outside sales team. Instead of wading through a complex CRM, Troops alerts simplify the documentation process by pulling it out of Salesforce and into Slack. Reps can record next steps, move deals to new stages, and otherwise manage CRM information by tapping action buttons on Slack prompts or using voice to text.

Challenge 2: There’s a Disconnect Between Outside Sales Reps and the Rest of the Team

It can be difficult to get important information to sales reps when they’re on the road. The same is true for keeping sales managers and other team members abreast of important, real-time happenings in face-to-face meetings.

When everyone can’t communicate detailed sales information and collaborate effectively on accounts, sales teams fumble handoffs, lose crucial context, and put opportunities at risk. They also don’t get the benefit of feeling part of a team. They miss out on knowing how other deals are progressing or feeling the collective excitement and satisfaction of getting a big win.

Solution: Make Information Easily Shareable Across Your Company

It’s not easy to stay connected when you’re on the road. When you pull important conversations into places where your sales reps and managers already are, the challenge becomes much more manageable. For many teams, that place is Slack.

Slack helps bring critical information, coaching insights, and the latest deal updates into the open where the entire team can collaborate. Instead of requiring your outside sales reps to wade through Salesforce to find the information they need, they can request it in Slack, or better yet, receive a contextual alert.

These alerts are especially important for sales reps on the road. They need regular updates to have more informed conversations with prospects and customers, but they rarely have time to chase them down. Likewise, team members back in the office might have trouble tracking down information only the rep knows.

A BDR, for example, might be dying to know how a prospect meeting went. Yet, an outside sales rep isn’t going to have the time or mental bandwidth to update the BDR while on the road. Sales teams can get around this by setting up automatic alerts that notify the appropriate BDR once a sales rep logs an update. This keeps everyone informed, ensures the BDR gets credit for a progressed deal, and helps build trust between the BDR and the AE.

At DoorDash, closing an account is great, but the real win is when the account goes live. There’s a lot left to do after signing on a new account. For example, say a rep signs on a new customer. They won’t get credit until after the customer has a tablet in-hand and their establishment’s menu and photos are live in the app. To help keep their reps excited throughout that process, they use Slack and Troops to send notifications of deal progression milestones to their reps.

“We will passively share information with reps like ‘Hey, their photos are done. Hey, their menu’s complete. Hey, the tablet arrived.’ So they can keep in the loop on things that they would otherwise have to dig to find out.”
win gong.png

DoorDash also uses contextual alerts in Slack to handle important field change requests. Their sales reps don’t have the permissions to handle addresses in the DoorDash system for compliance reasons. So, when a sales rep needs an address verified or updated, Troops shoots an alert over to their manager in real-time. This makes it easy to update the field in Salesforce from Slack, quickly getting the rep the information they need.

Likewise, DoorDash celebrates wins in Slack to bring their outside sales reps into the party. They may not get to bask in the glow of office-wide applause, but outside sales reps still get to feel valued as the entire company rallies around them via chat.

“[One of the main things] we use Troops for is celebrating wins. Say a sales rep gets the biggest restaurant group in Oklahoma City. That will trigger an alert in Troops, which pulls a celebratory GIF to let [everyone] know. It’s exciting.”
Request a Demo

Challenge 3: Outside Sales Reps Aren’t Staying on Top of Their Sales Pipelines

It’s easy to fall into the trap of focusing only on the most immediate priorities when you’re busy fighting traffic, chatting face-to-face with prospects, and trying to squeeze in a bite to eat .

However, outside sales reps typically deal with longer and more complicated sales cycles. This makes managing the long game all the more important.

Solution: Manage the Sales Pipeline With Preemptive Alerts

overdue close dates.png

Preemptive alerts allow outside sales reps to correct sales pipeline mistakes before they become problems as well as course-correct overlooked opportunities.

For example, preemptive alerts will automatically notify sales reps when a deal’s next step or close date passes. Teams can also set up alerts that trigger when a deal moves to a new stage despite missing information or is stuck in the same stage for X number of days.

Give your outside sales reps the opportunity to fix these sales pipeline oversights before involving management. This prevents these alerts from feeling punitive and lessens the workload for sales managers, allowing them to focus on recurring or bigger problems.

Say you know you’re going to take a snapshot of your team’s sales forecast five days into Q2, send your reps a prompt reminding them to clean up their pipelines and forecasting information several days beforehand.

Find an Outside Sales Solution That Saves You Time

“Time is our No. 1 asset. When we assess new tools or workflows, we get to the lowest level of detail and say ‘How much time did we save?’”

DoorDash gauged the usefulness of an outside sales solution like Troops based on how it gave or took up their time. Instead of getting bogged down in all of the potential success indicators, they went straight to analyzing how their outside reps and managers would actually use the new tool. In doing so, they asked a few key questions:

  • “How long does it take to log an activity this way?”
  • “How often will my team do this?”
  • “What is the opportunity cost of doing things like so? Would my time be better spent doing something else?”

This approach helped DoorDash hone in on how their team’s behavior and workflow would change and the impact those changes would have on productivity as a whole.


Join Our Webinar on February 26, 2020

Register for our webinar at 11 AM on February 26, 2020 to learn more about how DoorDash overcomes top outside sales team challenges!

Register for Webinar

Roque Versace

Written by Roque Versace

Chief Revenue Officer

Subscribe to our blog