The Top 4 Sales Challenges Keeping Reps Up at Night in 2015 (And What to Do About Them)

As a sales professional, you likely have a lot on your mind as you work to hit your ever-increasing targets:

• How can I get more prospects to take my calls and meetings?
• How do I build value and maintain momentum with multiple stakeholders?
• How can I keep discounting to a minimum and protect our margins?
• How do I fend off aggressive competitors and close more deals?

If these issues sound all too familiar, you‘re in good company. Sales reps across industries are facing the same set of obstacles, many of which are more pronounced than ever as we forge ahead in 2015.

The Data: New Research Reveals the Biggest Barriers to Sales Success

Each year, sales training firm Richardson surveys sales professionals across B2B industries to gauge the most pressing challenges impeding their performance. Their latest research reveals the four areas where reps are struggling most:

1. Prospecting: 21% of respondents identified gaining appointments as their #1 prospecting challenge. With buyers‘ attention increasingly scarce and fragmented, reps are finding it tougher than ever to secure those critical initial meetings.

2. Account Management: For 17% of reps surveyed, providing value to multiple stakeholders across an organization is the top account management hurdle. As buying groups expand and diversify, reps must navigate more complex webs of influence and competing priorities.

3. Negotiation: Procurement‘s growing involvement and customers‘ easy access to pricing intel have intensified the pressure on reps at the negotiation table. 15% of respondents pointed to gaining higher prices as their chief negotiation challenge.

4. Closing: With the rise of empowered buyers and low-cost competitors, reps are struggling to get prospects to sign on the dotted line. 13% of study participants named closing against a low-cost provider as their top closing challenge.

The data suggests that mastering the fundamentals – securing meetings, building relationships, negotiating effectively, getting deals done – is more difficult than ever in today‘s complex B2B landscape.

But just how pervasive are these issues? Are certain reps struggling more than others? Let‘s dig a little deeper.

Benchmarking Performance: How Do You Stack Up?

To help gauge the scope of these challenges, the Richardson team sliced the data by key demographics:

By Industry:

• Technology: Over 1/4 of tech reps (26%) are struggling most with negotiation, namely maintaining profitability in an increasingly commoditized market.

• Financial Services: Prospecting is the biggest pain point for 1 in 5 financial reps, who are finding it harder to gain a hearing with risk-averse buyers.

• Healthcare: Navigating new procurement processes and providing value to a widening array of influencers are top challenges for 23% of healthcare sellers.

By Role:

• Field Reps: Compared to their inside sales counterparts, field reps are 28% more likely to face difficulties gaining higher prices during negotiations.

• Account Managers: Unsurprisingly, account managers are 33% more likely to struggle with providing value to multiple stakeholders vs. their new business focused peers.

By Company Size:

• Organizations with $50M-$500M in annual revenue are 20% more likely to cite prospecting as a top challenge compared to their larger enterprise counterparts.

• Reps at sub $50M companies are 2X as likely to report providing value to multiple stakeholders as a primary account management hurdle.

Whether due to differences in resources, brand recognition, sales complexity or other factors, it‘s clear certain cohorts of reps are feeling the burn of these challenges more acutely than others. But make no mistake – these issues are impacting front line performance across the board.

Consider this:

• 67% of reps consistently miss their quotas (CSO Insights)
• 57% of the buyer journey is complete before a prospect‘s first interaction with a rep (CEB)
• 60% of qualified pipeline ends up in "no decision" or stalled deals (SiriusDecisions)

The consequences of not effectively addressing these challenges are dire. But the good news is they are not insurmountable. With the right mix of strategies, skills, and enablement, sales organizations can empower their reps to break through these barriers and drive better results.

Conquering the Challenges: 5 Strategies for Success

So what does it take to proactively tackle these common obstacles head on? Based on our work with sales organizations around the globe, here are five strategies we see the most successful teams employing:

1. Craft Compelling Value Propositions

Effectively conveying value in a way that resonates with each stakeholder is paramount to overcoming all of these challenges, from opening doors to expanding relationships to protecting margins to edging out competitors.

The key is to develop a deep understanding of your different buyer personas and tailor your messaging accordingly. Consider creating a value matrix that maps your solution‘s benefits to each persona‘s specific goals and concerns.

For example, an HR manager will care most about how your product streamlines their team‘s workflow, while the CFO will scrutinize the hard dollar impact. An IT buyer needs assurance your solution will integrate seamlessly with their systems, while the end user craves an intuitive interface. Articulating value in the language of each stakeholder is critical.

2. Prioritize and Personalize Prospecting

When it comes to breaking through the noise and securing meetings, it‘s about quality, not quantity. Focus on attracting your ideal customers vs. casting a wide net.

Start by partnering with marketing to develop an Ideal Customer Profile (ICP) – the specific characteristics of accounts that are the best fit for your solution. Then use predictive analytics and intent data to zero in on prospects that match that profile and are demonstrating active buying signals.

Once you‘ve identified a high-quality prospect, research them thoroughly. Reference their company website, social media profiles, published articles, and recent news mentions. Use these insights to personalize your outreach and demonstrate genuine interest in their business.

For example, you might reference a recent company announcement or highlight how your solution aligns with one of their stated strategic priorities. Or share a relevant case study or article that speaks directly to a challenge they‘re facing. Thoughtful personalization is key to getting a response in an inbox overflowing with generic pitches.

3. Collaborate with Customer Success

Delivering consistent value to an ever-expanding network of customer contacts is a team sport. It requires tight alignment between sales, account management, and customer success.

From the earliest stages of the sales process, work with your customer success counterparts to map the buying committee and develop a coordinated plan to engage, educate, and support each stakeholder. Some best practices:

• Set up a standing meeting cadence to share intel, discuss account progress, and troubleshoot issues
• Develop shared account plans with clear owners and action items for each relationship
• Create joint QBRs and other forums to regularly engage with customers and gather their feedback
• Celebrate successes and learn from losses together as a unified team

Bridging the gap between sales and post-sale will ensure a seamless customer journey and make you indispensable partners in their ongoing success.

4. Elevate the Negotiation Discussion

No customer relishes a price negotiation, and neither should you. The goal is to steer the discussion away from price and focus on the unique value you provide relative to alternatives.

Easier said than done, of course. But you can give yourself an advantage by:

• Building a strong business case that quantifies the ROI of your solution
• Emphasizing the intangible benefits like superior support, domain expertise, etc.
• Sharing stories/case studies of similar customers who‘ve seen concrete results
• Offering creative deal structures, bundles, or terms vs. straight discounts
• Providing choices that let the customer make tradeoffs based on what they value most

Remember, if you‘ve done the work to build trust and demonstrate value throughout the process, price should be a confirmation of that value, not a separate discussion.

5. Sell the Long-Term Relationship

In competitive situations where the prospect is weighing several similar options, reps often resort to discounting as a silver bullet. But the most successful reps take a different approach.

They know that in an era of heightened expectations and lowered loyalty, winning on price is a race to the bottom. What customers really crave are solutions that will drive results now and adapt as their needs evolve.

That‘s why top performing reps sell the long game. They spend time learning the customer‘s strategic objectives and paint a vision for how the partnership (not just the product) will support those goals over time. They talk about the investments their company is making in innovation, services, and support. They share examples of how they‘ve helped similar customers scale and adapt to change.

Ultimately, they make a compelling case for why the two organizations are uniquely suited to drive better outcomes together for the long haul. And that‘s a difficult narrative for any competitor to match.

The Path Forward

With unprecedented access to information, more stakeholders involved in decisions, and higher expectations than ever, today‘s B2B buyers have upended traditional sales models. Reps that fail to adapt their approach will continue to struggle with the very fundamentals of their craft.

But those that commit to mastering the new rules of engagement – leading with insight, tailoring their message, aligning their teams, elevating the discussion, and always selling the bigger picture – will be uniquely positioned to overcome these obstacles and emerge as winners.

As you work to conquer your own challenges and take your sales game to the next level, consider this:

• What are our ICPs and how can we use data/analytics to identify and prioritize our hottest prospects?
• How can we better segment our messaging and content to speak directly to each stakeholder persona?
• Where are the biggest points of friction in our customer handoffs and how can we create a more seamless experience?
• What unique value do we provide beyond features/price and how can we better quantify and communicate that value?
• How can we position ourselves as long-term strategic partners vs. short-term product pushers?

Regularly stepping back to ponder these questions will keep you focused on continually honing your strategy and skills to stay ahead of the curve. Because while the challenges may be daunting, for reps willing to put in the hard work of evolving their approach, the opportunities have never been greater.