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The Complexities of Collaboration in Sales

This article is part of a three-part series on Sales Innovation. Check out Part 2: Navigating the Pitfalls of Rapid Scaling, and sign up for our newsletter to get Part 3 sent directly to your inbox in the coming weeks.

Whether internal or external, collaboration is in the zeitgeist.

Companies are seeing collaboration as a creative approach to accomplishing more with less. From fashion to the future of work, entire industries are being reimagined through the lens of collaboration. Externally, adjacent players are scrambling to find each other and expand their reach through unique partnerships. And internally, software for collaboration is abundant, as are the playbooks for redesigning meetings, bringing disparate teams together, and driving more cross-functional moments. 

Yet this opportunity seems to elude many of the sales teams we speak with. In our research and conversations, we’ve found three areas that make collaborating, both externally and internally, so difficult within sales:

  1. The Job Description
  2. The Time to Scale
  3. The Culture

In this post, we’re going to focus on the first challenge we’ve run into:

The Job Description

Historically, Sales JD’s have been written with a heavy emphasis on individual performance and short-term wins, with the latter typically driving the former. This model made “cents” (pun intended) when sales were straightforward transactions and product knowledge was the currency of the sales person. That individual could unlock sales by framing their product’s unique aspects to a prospect and persuading them on its merits. Today, sales roles continue to reflect this model with a focus on efficiency to drive singular quick wins. 

But, as it does, the world evolves, demands shift, expectations change, and life gets more complicated. Products are rarely singular, decision makers aren’t individuals but layered committees, and businesses are evolving so quickly that one can barely keep up. Selling solutions in today’s world requires depth of industry knowledge, an expanded look at the buyer’s stakeholders, and an understanding of the unique set of challenges they’re facing at any given moment. 

According to Salesforce’s State of the Connected Customer Report, 84% of B2B customers expect sales representatives to act as trusted advisors and understand their goals, but 73% say most sales interactions feel transactional. There is a clear contradiction between what the customer wants and what the sales organization prioritizes. Below, we share a few starter questions we’ve used with our clients to help them begin to bridge this gap.


The standard sales job description no longer supports how a prospect wants to be sold and actively creates tension for sales teams. 

While there’s no easy solution to change a system that dictates people’s pay structure, the goal in our work with sales leaders has been to prompt conversations around the short- and long-term adjustments needed to close this gap. The same way product teams consistently test new features to improve product/market fit, piloting updates to these roles and responsibilities allows our clients to not fall further and further behind. 


1. Strategy Alignment

How well does our current JD align to the narrative our leadership is delivering to the sales org about goals and growth? What are the biggest gaps between the two? 

2. Client Understanding

How have our clients’ expectations shifted over the past few years? What do they care about today? What’s different?

3. Minimizing Gaps

How might we use what clients care about as prompts to rewrite our JD and focus on the new skills needed to deliver on our clients shifting expectations? 

4. Honest Expectations

Realistically, how well could a human deliver on the range of responsibilities and capabilities outlined in the JD? How might time and space for increased collaboration with SME’s help in delivering on this updated role?

For more on our work helping sales teams unlock collaboration, check out these case studies:

Collaborating in sales is hard work, and sometimes teams can use a little outside help. If you’re interested in learning how we might support your sales team or organization, send us a note and we’ll set up a discovery call with one of our team leads.

Jason Wisdom
[email protected]

Jason Wisdom is one of the co-founders and partners at The Design Gym, a strategy and innovation consultancy helping leaders to grow their business by fully unlocking the power of their most important advantage: their people. We work at the intersection of business strategy, experience design, and change management to engage the people that matter most to your work: your customers, your leaders, and your employees. See something that resonates with a project or challenge you're working on? Shoot him a note at [email protected].

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