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7 Ways Digital Natives Are Shaping Your Enterprise Selling Strategy


Problem: Digital natives are changing the paradigm and processes around enterprise selling faster than most C-Suite executives responsible for revenue can keep up. 

Opportunity: Adapt the sales experience to better utilize technology to support the discovery, evaluation, and decision-making stages to meet the expectations and habits of a new kind of buyer.

Resolution: Re-imagine new sales processes that take advantage of data, digital content, and multi-channel experiences that can be measured, adapted, and optimized over time.

Digital transformation is disrupting digital and non-digital businesses in ways that can no longer be ignored, dismissed, or explained away. There is no part of any business or organization that is experiencing this more regularly than those responsible for sales and marketing.


As digital natives flood the buyer and seller roles inside enterprises, what B2B selling has looked like in the past is going to shift dramatically.

The person most likely to have access to enough data to see this transformation and its impact on revenue creation sits too far removed from the tension of the marketplace. Therefore, he or she is most likely to underestimate the urgency or demand for change.


But those leaders responsible for the day-to-day effort to find, qualify, and close accounts know the habits around enterprise selling are grounded in assumptions that are no longer true and practices that are no longer as effective as they have been in the past.

Three Variables Are Driving This New Reality.

  1. The growing presence of digital natives with the enterprise. Digital natives may not have flooded the C-Suite yet, but they are populating enterprises faster than non-digital natives. It’s only a matter of time before their personal preferences, habits, and efficiencies dramatically shape the buying and selling processes in material ways.

  2. The consumer mindset is influencing the enterprise buyer. B2C and B2B selling are still distinct categories of selling, but the divide between the two is shrinking. With a greater emphasis on customer experience, a more integrated, multi-channel, and holistic strategy will be required to win in the enterprise settings moving forward.

  3. The presence and access of data available to decision-makers. Data provides sales leaders and seasoned executives the opportunity to exchange gut and personal bias for actionable insights that lead to more effective, efficient, and productive sales cycles. The bias of past experience can really hurt if you don’t allow your assumptions to be challenged or validated by data.

7 Ways to Retool Sales Support Systems for Digital Natives

  1. Champion your CRM. No salesperson likes a CRM. But it’s even worse if your CRM is just an extra tool that is perceived as a benefit to management but an interruption to those in the field. Build and adapt your CRM to better inform prioritization and commitments of those in the office and in the field. Use it as your foundation as your coach your team to success. And make sure your CRM is mobile-centric, or you’re done before you even get started.

  2. Deliver product marketing in an on-demand environment. Stop printing a forest worth of product marketing when your buyer is just going to scan in your information and keep it in an electronic format for review and reference. Enterprise buyers are mobile-first given the fast-paced nature of their roles. Start making your product marketing inventory of options available to your sales team instantly, so they can pivot in the moment of the conversation rather than a day or two later.

  3. Invest in enterprise content marketing to support a buyer who doesn’t want to engage a salesperson until they have the information they need to shape the experience they want. The buyer no longer needs the seller to inform them of their options. The buyer needs a seller who can appropriately challenge or validate what they believe to be true. To accomplish this will require an interdisciplinary and cross-functional effort. The benefit will be much more qualified leads and an overall reduction in time to contract when applied correctly.

  4. Define your buyer’s journey and apply sales funnel metrics to every stage. This will inform what assets and experiences will be required to build connection, affinity, and trust over time while also building in the ability to measure the effectiveness of sales and marketing tools and processes instantly so you can adapt quickly. Your gut about what works and what doesn’t is probably wrong, so commit to using data to inform your commitments and operational allocation. 

  5. Use account-based selling and marketing as your business development accelerator. The idea of building an entire enterprise strategy around one client used to be absurd—if not impossible. But the competition for enterprise contracts and budget commitments is growing fierce. Buyers want a compelling and contextual buying experience that demonstrates you know them, their business, and their challenges before they will invest their time to engage with you around your products and solutions. 

  6. Evolve sales management from structured motivation to individual success planning. Weekly sales meetings and quarterly performance reviews aren’t enough in a dynamic landscape like enterprise sales. Design a tiered mentorship experience that affords an ecosystem of internal support that will ensure success for every member of your team. Don’t just manage by lagging indicators of pipeline and contracts. Incorporate leading indicators of campaigns, contacts, buyer personas, industry or vertical realities, and organizational characteristics, too. As new insights are available, share them with the team and make it easy for them to integrate into their decision-making framework.

  7. Make personal branding a priority. If your team isn’t building their digital identity, you will not be able to overcome a digital native’s desire to know whom they are buying from as well as what they are buying. Social signals influence our consumer decisions. The same is becoming true for enterprise decisions. It’s becoming more and more difficult to stand out from your competition except for one specific area. The only thing your competition doesn’t have is your people. Use that to your advantage. (And if you’re worried if personal branding success will inhibit your ability to retain talent, you’ve already lost them.)

The Complex Sale Still Requires Human Intervention

It’s going to be a long time before robots can reproduce the wisdom and discernment humans can. So for the foreseeable future, your enterprise sales team will remain a necessary part of driving business development and revenue initiatives inside the enterprise. But that doesn’t mean you get a pass on how digital transformation is disrupting operational and management effectiveness.

The growing presence of digital natives will eventually disrupt much of what you consider normal. As they make their way into the C-Suite, it will fundamentally change your entire enterprise and culture tomorrow.


Get ahead of your competition by doing what many won’t be willing to do: measure, learn, and adapt.

If you will, you will “make it rain” consistently through a more digitally-centric and data-driven approach that will yield smarter decisions and more effective use of your human resources than what was previously thought possible.



Ben Stroup is Chief Growth Architect and President at Velocity Strategy Solutions where he helps leaders design, develop, and deploy smarter business growth strategies. Ben is a futurist, disruptor, and data champion. He leads a team that takes a structured learning approach to business challenges, which allows them to assist leaders in bridging the gap between ideas, innovation, and revenue—taking ideas from mind to market.

Velocity Strategy Solutions is an on-demand, next-generation business strategy and management consulting firm which provides clients with a relentless focus on data, execution, and results that positively impact the bottom line. Velocity delivers integrated people and revenue strategies combined with a disciplined approach to growth architecture that elevates the capacity of leaders, teams, and organizations to succeed and win more.

Topics:   Growth