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The Agile Revenue Organization

Change is inevitable. Change is constant. Change is permanent whitewater. We've heard these exhortations before. But it's never been more real than today. Companies must adapt faster and smarter than ever before. In short...the agile company wins. More than just winning in the moment, the agile revenue organization is a sustainable competitive advantage.

The purpose of this brief is to explore how B2B companies are implementing an agile approach and culture across the functions that create revenue: Leadership, Marketing, Enablement, and Sales.

Agile cross functional teams are good at embracing the reality that B2B sales and marketing will be forced to continuously adapt to change at a faster pace than we ever thought possible. While “I can’t wait to get back to normal” was uttered by everyone, very few believe we will ever revert back to how businesses made purchasing decisions.

An obvious driver is the pace of innovation and digital transformation which are central to the business strategy for companies in every market segment. So how does the revenue organization coordinate strategy and build a culture that can stay agile in the face of disruption and new market opportunities? The first step is to fully accept that the business, marketing and sales strategy for every company will need to continuously adapt going forward.

External forces combined with market opportunity create the need for an agile model across the revenue organization.

Agile Leadership

Agile leaders expect change will occur and they actively pursue opportunities tied to those inevitable market shifts. This agile leadership mindset happens across multiple levels and functional leadership positions including CEOs, sales leaders, marketing leaders, and product leaders who balance between long-term business strategy and short-term sales plays. For most organizations, the business strategy and a handful of core plays are the backbone of the revenue model. Think of core plays as the standardized ways a company wins new business and grows each account over time. Core plays stay fairly constant.

Agility comes into play through more dynamic and situational plays. Dynamic plays are tied to immediate market opportunities like the decline of a competitor, a shifting pandemic, a merger, a new product category, or a new partner relationship. The power of the dynamic play is the in the ability to quickly refocus a sales team on a strategy that can impact the business in the near term.

Situational plays are more tactical than core and dynamic plays. A situational play gives the seller the agility to change direction for a specific sales opportunity or meeting based on the reality of that selling scenario. With the right situational approach, a seller can quickly align to the buyer role, the customer initiative, or a specific type of conversation.

When senior leaders embrace the concept of sales plays, they create a repeatable model for aligning the broader organization. Across DSG client organizations the most agile leaders embrace their role in constantly managing risk, move quickly when market opportunity emerges, and develop the organizational capacity to adapt.

Example CORE PLAYS (focused on hitting the revenue target)

  • Land new business with one of our 3 core solutions

  • Expand existing accounts by cross-selling these 5 offerings

  • Sell the comprehensive platform within these 4 verticals

Example DYNAMIC PLAYS (tied to market opportunity)

  • Win back accounts from that competitor based on the competitor’s lack of innovation

  • Cross-sell a strategic new product into all existing accounts with a specific profile

  • Position a multi-product, integrated solution in “Top 100” accounts

  • Re-position the brand as an integrated solution provider in both net new and existing accounts

  • Pursue CFO conversations focused on total cost of ownership for all renewal customers

Example SITUATIONAL SALES PLAYS (specific to a live sales opportunity or meeting)

  • Marketing leader looking to get educated on AI in the retail space and engaging our top competitor in parallel

  • Buying committee engaged us at the RFP stage with misaligned requirements and we need to reframe the solution needs vs. respond to the RFP

  • Existing customer is not hitting their targeted outcomes and we have 9 months before renewal opportunity

  • CFO is directly engaging around total cost of ownership and is clearly in the midst of defining requirements

Agile Marketing

The agile marketing leader knows how to connect upstream marketing and campaigns with downstream sales conversations. It’s one thing for senior leadership to prioritize a dynamic, innovative strategy for Q3 and Q4. The real work begins when marketers take that sales play and turn it into the content, tools and campaigns that will begin creating engagement.

A critical success factor for marketing is the translation of their macro view of the total market, market positioning, market perception, and competitive realities into practical content for sellers in every channel. A common accelerator for this translation is bringing senior marketing, product and sales leaders together to debate and align on how best to operationalize each core, dynamic or situational sales play. That cross-functional collaboration results in the insights, talk tracks, and customer-facing visuals that make it easy for a seller to make things happen.

The sales conversation divide is non-existent in organization where marketing drives focused sales plays tied to actionable content and tools.

Let’s say that marketing is tasked with turning a new dynamic play like “cross-sell a strategic new product” into a multi-channel campaign that will churn out leads ready for sales pursuit. For the agile marketer, the idea of misalignment between sales and marketing is a myth because marketing, sales and enablement leaders were connected on the path to sales execution from the moment the play was given the green light. Where some organizations experience a sales conversation divide between the marketing strategy and every day selling conversations, that divide is eliminated when marketing takes responsibility for the actionable side of sales plays. A repeatable approach for marketing and enablement to stay in sync on how to equip the sellers on each play is to realign on customer buying process framework semi-annually.

Agile Enablement

Agile enablement leaders see themselves as the catalyst for equipping sellers to implement prioritized sales plays that will drive tangible sales outcomes. Some of the most respected enablement leaders DSG has had the privilege to engage are directly collaborating with senior leadership to align all content, tools, and training to the business strategy and focused sales plays. When enablement leaders evolve their programs based on what’s being prioritized, those same leaders quickly become viewed as catalyzers who turn strategy into results.

Sales plays tied to microlearning has quickly become the preferred model for aligning enablement to the needs of each user and their specific challenges and learning gaps. Traditional learning courses that force the learner to consume content from beginning to end are finding a reluctant and weary audience across every sales channel. There just isn’t enough time or patience for traditional long-form LMS modules.

The consumer experience of getting great content via a YouTube search is having a profound effect on what is expected at work. Just-in-time learning is what we’re doing at home so we come to work looking for the same experience. Sellers find themselves hungry for short, focused, practical videos on topics that are relevant to their next sales conversation. The resulting disruption for the enablement team extends well beyond the learning experience and includes internal pressure to financially justify every system, prove business impact, and keep sales productive and happy.

So where do you start? A practical framework for re-engineering the content and training through a microlearning approach is to begin with the customer buying process. The customer buying process or buyer journey is useful because sales and marketing can typically agree on how the customer engages the sellers and the ways we could have more influence on that decision process. The buying process becomes a forcing function to eliminate everything a seller might need “just in case” and provide them with exactly what they need “just in time” based on the buying process stage, customer persona and level, customer initiatives, and any competitors involved in the opportunity.

Enablement leaders are able to catalyze sales plays through a customer buying process lens which forces decisions on the internal sales education and external customer-facing tools that will make salespeople smarter and drive sales outcomes at each stage of the buyer journey

Agile Seller

Agile sellers are continuous learners who need useful content for their next sales conversation in 4 areas:  what to know, do, say, and show

The agile seller is a unique breed that represents the future of B2B selling in a constantly changing environment based on:

  1. Go-to-market strategy shifts for the business

  2. Evolution in how customers buy solutions

  3. Near-term market opportunities

  4. Uniqueness of any given selling scenario

It’s helpful to look at the DNA of an agile seller across a handful of disciplines every seller can master:

Continuous Learner New knowledge and insight must be quickly learned and mastered as the organization aligns around new sales plays and shifts in business strategy. The agile seller knows the path to excellence has no finish line.

Ready for the Pivot Any given sales conversation may require a specific sales path based on the customer’s unique dynamics and focus. The agile seller is ready to make the shift to a different sales strategy, discussion topic, customer story, specific use case, or a new line of discovery based on their situational awareness.

Hungry for Coaching Learning something new means it must be practiced. It won’t be mastered the first time around and, in fact, may have to change midstream. Embrace the coaching to continue to build on what you are learning.

Constant Communication

As the organization goes through rapid cycles of change, communication is critical. Feedback from sales specific to what is or isn’t working in real client conversations flows back through the organization with as much automation as possible.

Outcomes Aligned

With each initiative the organization tries, early indicators of success let leadership know if the direction is sound. The agile seller stays fully aligned to the outcomes for the organization and the outcomes for the customer.

Bringing it All Together

Here’s a cheat sheet for the big ideas across each function in a thriving agile revenue organization.


  • Balance long-term strategy vs. opportunistic

  • Orient management around outcomes and measurement

  • Develop organizational capacity for change

  • Create clarity on sales and marketing integration

  • Translate the macro strategy and market insight into sales ready content

  • Bridge the sales conversation divide

  • Build practical sales content and situational talk tracks

  • Make storytelling easy for sellers

  • Be prepared to pivot based on the situation

  • Stay laser focused on aligning to customer outcomes

  • Adopt a continuous learning mindset

  • Embrace and push for coaching and feedback

  • Catalyze sales activation for prioritized plays

  • Prioritize and simplify content and tools for sellers

  • Align sales content and training to the customer buying process

  • Accelerate the shift to microlearning