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Sales Best Practices

The Top Sales Engagement Challenges and How to Overcome Them

Cari Murray's Avatar

Cari Murray

Senior Manager of Content Marketing

Sales engagement is at the top of everyone’s priority list — from sales managers to Chief Revenue Officers — and organizations are investing in it, now more than ever.

Roughly 90 percent of sales leaders plan to invest in technologies and methodologies to help sellers better engage with prospects and customers, according to Gartner (formerly TOPO), a research and advisory company for sales and marketing executives.

What has helped everyone finally see the light? When your sales engagement strategy is working, you will see it in your bottom line.

But what happens when it is not working? How do you pinpoint your barriers to success, overcome them and meet sales goals as a team?

For many go-to-market teams, the challenges are the same. Gartner identified these challenges in its recent Sales Engagement Leadership Report. The data from that report was based on Gartner’s sales engagement survey, which was completed by 100 sales and marketing leaders at high-performing organizations. Their roles were primarily vice presidents, directors and managers so they’ve experienced these challenges first-hand.

Here are some of the top challenges identified — and Outreach’s strategies to help you overcome them:

Challenges No. 1 & 2: Content Strategy and Partnership with Marketing

Roughly 41 percent of respondents identified “content strategy” as a challenge.

It came in head and shoulders above the other challenges, followed by “partnership with marketing” at 26 percent. It makes sense that these two claimed the top spots.

Too often, sales and marketing end up working in silos, with little collaboration. Sales engagement is typically owned by sales, whereas content strategy is owned by marketing. This becomes a problem because insight and resources are not shared cross-departmentally.

Solution: Make sales part of your content strategy + create a shared internal content library

Factoring the sales team into your content strategy would actually benefit both. For example, who fields all of the questions from prospects? Sales.

That means they have invaluable insight into what questions your target audience often asks during the sales process. This could inspire a really tailored FAQ page on your company website or topics for a blog post. Sales could then leverage those same pieces in their process. The next time a prospect asks that same question, they don’t have to spend the time writing a custom reply. They have approved messaging and the right piece of content to help educate the prospect.

Another example of potential collaboration might be a marketing-driven “key messaging” document for new product or service rollouts, to help sales plug-and-play that well-crafted content into their prospect emails.

Consider calendaring a recurring, monthly meeting between sales and marketing where the question is prompted: “What content pieces should we be creating to aid in the sales process?” Your organization might also consider creating an internal library of this content that both sales and marketing can access, which creates consistent messaging. Bonus, if you can enable sales with this key messaging and proven content in real-time while they’re in meetings.

Challenge No. 3: Effective Sales Engagement Playbook + Process

Twenty-five percent of respondents found it challenging to build an effective sales engagement playbook and process.

Based on feedback from our own customers, we’ve found that sales teams struggle with this at two levels. The first is a lack of visibility into the effectiveness of their current efforts. Second, they don’t have streamlined playbooks and processes.

Ask 12 sales reps how they handle an objection, such as “it’s not the right time,” and you will likely get 12 different answers. Sales managers need to be able to see the actions their sales reps are taking, but also the effectiveness of those actions.

Solution: Develop a sales engagement playbook and measure its success

You want your sales reps’ success to be predictable — and scalable. It starts with developing an effective sales playbook.

Some key elements to include:

  1. Ideal Customer Profile (ICP) and buyer personas
  2. Stages in your sales process (discovery, product demo, negotiation, purchase decision, etc.)
  3. Common touch points and engagement channels (email, phone calls, social messaging, etc.)
  4. Customer demographic (size, location, industry)
  5. Marketing and sales collateral (web content, guides, webinars, industry reports, podcasts, call scripts, email templates, etc.)
  6. Prescribed sequences and workflows for each specific sales scenario
  7. Metrics and means of measurement
  8. Technology stack (CRM, Sales Engagement Platform, etc.)

Playbook performance should be monitored and optimized along the way, adopting the approaches of top sellers on your team. You can see the activities your top sellers engaged in and what sequences (workflows) led to meetings booked in Outreach’s Team Performance Dashboard.

Outreach’s Team Performance Dashboard

Outreach’s Team Performance Dashboard

You can then take that insight and scale what is working across the team. That lifts productivity, accelerates your sales cycles, and positions your organization for sustained growth.

Challenge No. 4: Defined Sales Engagement Strategy

Ambiguity is one of the biggest barriers to a successful sales engagement strategy. That is probably why a defined sales engagement strategy was a challenge for 25 percent of TOPO’s respondents. You need everyone on your team — from your newest rep to your most seasoned one — rowing in the same direction. To do that, you have to have shared goals. Otherwise, everyone is moving without any real destination and is likely just going in circles.

Solution: Plan, analyze and optimize your sales engagement strategy

Every plan starts with a goal. What sales engagement metrics tie back to your desired business outcomes? For example, one of your sales goals might be increasing meetings booked by a certain percentage, quarter-over-quarter.

Outreach allows you to measure Key Performance Indicators, like meetings booked, at a glance. That makes it easy to create concrete sales engagement goals and incentivize them internally. Your sales engagement strategy should also take into account communication channels, content management, automation, engagement tracking, and optimization.

Sales engagement is not a “set-it-and-forget-it” strategy. It should be dynamic, allowing you to assess the results and adjust accordingly. That refinement can help transform challenges into opportunities that position your sales team for success — and your company for financial growth.

To learn more, this e-book that explains 3 key considerations to ensure sales and marketing teams are aligned.