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Remote Selling: 5 Ways to Win in 2023

B2B Sales Rep Doing Remote Selling

In light of all the “return to the office” buzz, it’s natural to wonder what it means for remote and hybrid sales. 71% of B2B buyers prefer to work remotely, and Gartner predicts that 80% of all sales interactions will be digital by 2025. In other words, you can’t take your foot off the gas when accelerating your B2B remote selling strategies. 

To set remote sellers up for success, you’ll need to equip them with new ways to build trust (and pipeline) with little or no in-person customer interactions. As a front-line leader, you’ll need to find effective ways to prioritize team engagement and foster camaraderie despite the distance.

More technology will not necessarily solve remote selling challenges. However, your team will need tools that eliminate distractions, prevent overload, and allow them to spend as much time as possible doing the job you hired them to do.

In this post, we’ll outline the top five remote selling challenges revenue teams face today and strategies to overcome them. 

Remote Selling Challenges Solutions
Building trust without in-person contact Automate touchpoints to nurture accounts and collaborate across teams
Managing and coaching a distributed sales team Prioritize team engagement and collaboration
Skill development and career progression Use metrics and KPIs to increase visibility and acknowledge rep performance
Fostering a collaborative culture among a distributed team Implement collaboration tools that foster culture and connection
Distractions and too much time spent on admin tasks  Eliminate context switching


1. Building trust (and pipeline) without in-person contact

When it comes to remote selling, the two biggest challenges reps face are preventing revenue from slipping through the cracks and keeping buyers engaged throughout longer enterprise deal cycles.

Although 55% of buyers report that working remotely has made their purchasing process easier, selling remotely still has its challenges. In an unpredictable B2B buying landscape and an unstable economy, it can take up to 27 touches to close a deal. 

Potential roadblock:

Switching back and forth between windows and apps, from call to email to Salesforce, drains reps’ productivity and creates more opportunities for revenue-generating tasks to be overlooked. Even worse, many teams still use spreadsheets to collaborate across departments, making assigning action items to different roles impossible.

Unfortunately, valuable opportunities to build trust are lost in digital interactions, making it more difficult to keep buyers engaged throughout long deal cycles. For example, tone is often misinterpreted via email or text, making sensitive conversations like negotiations fraught with potential pitfalls. On top of this, the follow-up needed to nurture accounts can quickly become overwhelming.

Try this strategy:

Sellers can prevent dropping the ball by using a sales engagement platform to automate the touchpoints that nurture accounts and enable easier cross-team collaboration. To keep buyers engaged throughout the deal cycle, all tasks, messages, and follow-up items should be pre-set, with reminders telling reps what they need to act on next. 

A sales engagement platform enables your team to easily set up automated messaging and workflow rules to automate actions such as:

  • Creating tasks to follow up with a lead 3, 7, and 14 days after the lead is created
  • Automatically sending an email a few days before a prospect’s trial expires
  • Change a status field if there is no activity for more than 30 days

Salesforce Workflow Management

When you implement a sales engagement platform that allows managers and reps to assign Salesforce tasks directly to other team members, you give your team a visual, interactive way to collaborate versus working out of spreadsheets. 

You’ll finally make your reps’ workday easier by giving them the ability to perform and log tasks from where they’re already working. Sellers no longer have to jump from app to app when they can automatically log inbound and outbound emails to Salesforce right from their inbox. Or, set up automatic activity tracking to make sure all activities are syncing back to the appropriate contact, opportunity, and account in the background.  

Email, Calendar & Activity Tracking

2.Keeping distributed sales teams engaged by prioritizing transparency and communication

Even the best sales managers have a learning curve when acquiring the leadership skills needed for remote or hybrid teams. Lack of face-to-face interaction will require you to be more intentional about the frequency of contact and communication mediums with your team.

Potential roadblock:

Remote teams often struggle with a lack of community and camaraderie needed for sales success. Reps need guidance on which deals to prioritize and the next best actions to take to make progress on those deals. Managers need insight into what their reps struggle with to know where to focus their coaching

Try this strategy:

To gain visibility into reps’ activities, you need the right systems to track their activities and review their performance for coaching opportunities. Implement a sales engagement platform with conversation intelligence capabilities to capture critical insights and analytics from phone calls. Granular insights allow you to influence the conversation and drive better business outcomes — even from afar.

To break communication barriers, lean on tools that enable quick, informal messaging like Slack or Microsoft Teams. Use data from your conversation intelligence (CI) platform to provide actionable feedback to your reps. CI data allows you to spot trends and patterns like mentions of competitors, commonly heard objections, and feature requests that would be helpful for your product team. 

Groove Conversations - review transcripts without leaving your workflow

3. Enabling skill development and career progression

Reps lose the opportunity to learn faster and establish mentorship relationships when working on distributed teams. Remote salespeople are left to their own devices to gain critical selling skills without the ability to listen in on their colleagues’ calls, walk over to their manager’s desk, or join one-off strategy sessions.

Potential roadblock:

Even though work-from-home is all the rage for the foreseeable future, there’s no denying that building relationships and proving effort takes a hit when work isn’t visible. Visibility obstacles can put team members years behind on their career trajectory, ultimately making them hesitant to join remote teams in the first place. 

Try this strategy:

To create a highly engaged team, ensure each team member knows what you expect of them. The most clear-cut way to define and communicate expectations is through metrics and KPIs. Don’t stop there — once expectations are set and understood, lay out a clear path that shows reps how these goals contribute to the higher-level company objectives. 

To ensure that reps are acknowledged and rewarded for a job well done, use a sales engagement platform that automatically captures all interactions across email, calendar, LinkedIn, phone calls, and video conferences. For example, you could use CI to hear how your top performer is successfully handling an objection, then share those best practices with the rest of the team.

4. Using collaboration tools to foster a connected culture

Sales culture is built around reps coming together and participating in team-building activities. Studies have found that remote work puts company culture at greater risk, with employees reporting feeling lonely and unsupported by their manager and team.

Potential roadblock:

Without the ability to do in-person one-on-ones, QBRs, and forecast calls, building rapport and ensuring reps get the proper support and assistance they need is a challenge. When departments don’t feel connected and can’t efficiently collaborate, customer relationships (and ultimately revenue) suffer. 

Try this strategy:

Managing a sales team is more than just setting and achieving sales goals — it’s about cultivating relationships with your team. To establish stronger team relationships, don’t be afraid to over-communicate. Ensure the entire team knows what needs to be accomplished and how they will get it done. Giving them the ability to see their goals and progress at a glance is key to goal attainment.

Groove Insights Feature for Salesforce Reports

To improve team collaboration, make sure you’re able to share real-time updates and changes. Whether your company has full-cycle sellers or employs teams of SDRs, AEs, and account managers, they should all be able to see what’s happening in an account to ensure everything is on track and offer input to help move the deal down the funnel.

A Salesforce-native engagement platform allows managers and reps to easily assign tasks to other team members to collaborate on opportunities and accounts in real time. By eliminating siloed spreadsheets and static data that is difficult to share and update, you’ll accelerate deal cycles and close more business.

5. Cut down on distractions and time spent on admin tasks  

Reps spend their days jumping from LinkedIn to email to calls — all while being bombarded by endless Slack pings, dozens of open browser tabs, and back-to-back meetings. With only 41% of the workday spent actually selling, it’s no surprise that there’s no time to focus on their highest impact work like building quality pipeline.

Anatomy of Work Global Index 2022

Potential roadblock: 

Context switching is the latest distraction-laden phenomenon plaguing remote workers today. Switching back and forth between several unrelated tasks decreases the quality of our work, overloads our brains, and makes us less productive. For companies employing an army of seasoned sellers, any successful platform initiative will revolve around how easy the system is to use and incorporate into their workflows. For sellers used to doing things their own way, their willingness to change can be a major factor impacting adoption.

Try this strategy:

By now, most revenue teams have embraced sales technology to help reps easily accelerate and optimize emailing and prospecting. However, many reps still perceive tools like CRM as “extra clicks” and data entry that winds up benefitting management more than anyone else. 

You can decrease context switching and increase CRM adoption by enabling reps to access and update CRM data while working out of their inbox.

To decrease context switching even further, look for a sales engagement platform with native Salesforce integration. This allows your revenue operations team to customize the Salesforce data each user sees within their email or calendar based on their specific role. 

Sales reps need access to different fields than account managers, so make sure to customize their view of Salesforce data with the fields that are most relevant to their day-to-day activities.  By choosing a provider that serves as a layer on top of Salesforce instead of need to sync to a secondary database, you also avoid issues with inaccurate or missing data due to latency and sync errors.

Access Salesforce and LinkedIn from your Inbox Image

The bottom line on remote selling 

Whether it’s keeping buyers engaged throughout complex deal cycles, or keeping sellers connected despite a distributed sales force, hitting your revenue targets remotely comes with its own set of challenges. 

However, with the right strategies and technology, you ensure that your customers get the attention they need to stay loyal and that your team remains motivated to hit revenue targets. 

With so many collaboration tools available today, it’s easy for reps to become overwhelmed. You can combat this with sales engagement strategies that lighten your sellers’ load, allowing them to focus on their highest impact work.

Ready to arm your sales team to operate at peak performance? Learn how Groove improves sales productivity and quota performance. Schedule a demo today.

G2 Fall 2022 Grid Report - Sales Engagement Software

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