Why and how to digitalise your sales organization


Why and how to digitalise your sales organization

August 29, 2023
SUMMARY. Digital sales is about organizational change and a lot more than putting new customer channels in place and doing some digital marketing. Still, transforming traditional face-to-face driven sales to digital-first can be a challenging effort over multiple years. Sales is one of those functions where “the tried and proven” tends to stick for a long time and utilising new digital processes, customer data and tools does not necessarily come second nature. In this article, we get into what drives sales org digitalization, what kind of challenges there are and how to prepare for success.


The two major forces that drive digitalizing sales are changing customer expectations and technology disruptions. Oftentimes, we might miss the fact that B2B buyers are similar shoppers and social media users as everyone else outside working hours. According to a Gartner survey, 83% of B2B buyers prefer ordering through digital commerce (1)

Recognising the convergence of B2B and B2C experiences means that ecommerce store user interface design has to be taken seriously. While B2B buyers still buy ‘for a need’ rather than ‘on an impulse’, a great storefront experience can make all the difference when the buyer is busy, making orders on their mobile device in the middle of a construction site. 

Besides better storefronts, buyers expect personalized engagements with sellers. This is where data and technology can be a point of leverage already now. Automating data gathering from disparate systems to piece an unified customer profile, and processing that data to concrete action points will enable the personalized discussions. Salespeople can unlock new levels of productivity by having more time to focus on value-adding encounters. 

All business processes in future will be collaborative, data and AI fueled, bringing digital closer to the real world. However, simply by making something available, whether it is a new digital commerce storefront or new CRM tool, cannot ensure its use. 


Digital sales changes everything. Starting with how you interact with customers, how you organize teams, and manage talent. Coordinating the change from initial vision to concrete roadmaps, while balancing the short and long term, impact and efficiency, is not a one-man show. Transformation happens when you both start strong and maintain a continuous evolution of responding to customer, business user and technology needs.

The first type of companies never really start their journey. We get it, it is a huge initiative with a lot of change management. The companies that fail to begin, are sometimes hesitant until they have to start – that is, once they start actually losing the market to competition. At that point, there is temptation to do a big renewal at once and take the hit that some people might jump ship on a fast and forced change.

Most companies get going strong, but progress is so slow that confidence is lost. These companies struggle with mastering the digital sales skills and the necessary mindset. While the adoption of technologies might have been swift, the change in processes might have been haphazard. These companies learn through challenges that it is much more challenging to make new ways of working stick, than to implement a new technology. 

The third type of situation is one where lots of success is gained at first, but over time sales processes and structures fail to evolve into sustainable systems that remain in use and continue to offer value. Developing digital sales systems is a continuous effort on business and technology sides, and a healthy balance between new processes, new code, and maintaining core systems should be in place.

Then there is the less often discussed type where you have too much focus on  short term customer and business impact over long term efficiency. While you keep business engaged in continuous evolvement of the systems, you need to balance with efficiency of maintaining a system that can still evolve in future. Development of digital sales solutions and architecture is a key for making sure you can respond to new changes faster than your competition. Maintaining and refactoring code and, for example, bloated CRM setups can be overlooked, until implementing simple improvements takes twice as long as it used to. 


Successful digital sales transformation starts with leadership. Sometimes, digital sales can begin as ‘skunkworks’, something which is done on grassroots level to get new business units up and running. But rarely does that type of approach work for digitizing existing sales organizations. Executive sponsor who is accountable for success and ensures budget and resources is needed right from the get-go. 

Any good initiative begins with solid preparations. 

A comprehensive checklist of steps to prepare the organization might look something like this:

  • Name executive sponsor
  • Name a business owner for the initiative, someone who can span the boundaries across functional areas as a leader
  • Articulate the business case
  • Define key performance indicators
  • Identify overlaps with other initiatives
  • Create governance framework for the initiative
  • Form a cross-functional team including user representatives
  • Conduct agile training
  • Identify needed process changes and mindset changes

Once you start implementing the initiative, it is important to get some kind of shared concept of minimum viable product – ie. a clear answer to what kind of setup is needed to validate the new digital sales approach. Development should be organized in agile sprints where items are designed, built, deployed, and after deployment, learnings are gathered for next iterations. The core team is running the sprints and having demo sessions with a broader audience to get feedback during the development.

In co-creating with future end-users, there should be a named user representative who has the final say in cases of disagreements within an early experience user group. This representative does not need to be first-line manager, although you do need buy-in from them. When demoing and user testing, it is important to keep in mind different levels of skill in digital sales and technology in general. While digital developers love features and technical quirks, conducting case-based user testing, training and support is the way to go with non-technical audiences. 

Your salespeople are less likely – than maybe more digital-savvy marketers, for example –  to understand and comment on any underlying technical processes, but your digital sales development team can take steps toward the field. Consider the following case as an example.


The organizations sales leadership faces a situation wher on business unit had set up their sales a completely separate CRM system from the organization's core CRM. This happened due to misalignment in core CRM development and ramping business units operations, leading to the CRM not being tailored to their process The sales leadership had recognised major bottlenecks in the processes sales teams spent on moving data manually between their main CRM and the temporary system in use. On top of that, the contract and fulfillment processes were loosely linked to the sales process, cutting visibility of anticipated workload at the end of each month.

Business case for the initiative to migrate the business unit to adopt the organization-wide CRM was formed and the executive sponsor assigned a business owner and a team of early experience representatives, a pilot team, for the initiative. The work began with a design sprint covering the current ways of working and reflecting that on the anticipated changes plus added value that can be easily implemented within the core system.

During the project's governance meetings, it was uncovered early on, that certain salespeople have more technical proficiency and can communicate needs better than others, and the executive sponsor made possible that time is secured operational work to ensure quality project involvement. It was also recognised that while sales reps had gotten to use the temporary system, they had also started to feel the pain of inefficiency.

The most important goal for the implementation was to keep the sales process tailored to the business units needs, and implement something that is more efficient than in the previous system, to ultimately drive bottom-up adoption. However, sales representative feedback showed that the efficient process was not something they paid attention to - but were actually delighted by a particular data visualisation feature which the development team thought to be merely an add-on.

To further discover needs that might have been difficult to conceptualize by the salespeople, the solution development team participated in shadowing and jumping into salespersons shoes in the form of a field day. All of this fed into streamlined user experience for the salespeople, a seamless customer experience due to salespeople utilizing always up-to-date data, and a frictionless process orchestration to contract and order management.

After training the solution to a larger audience, the early experience team members took ownership of the system and became champions within their teams to drive day-to-day adoption. New users came with new thoughts and the early users funneled the thoughts to new development items to develop the system continuously.


Adopting a customer-first mindset is key when driving digital sales impact. But many times, the user experience of the systems implemented can be disregarded. Ultimately, it is our sales people using those systems that drive customer engagements. Focusing on greater digital sales adoption means treating front-line employees as users to whom we also optimize internal systems is also a key to greater efficiency.

Here’s a summary on how to get started:

  1. Start with a vision and clear roles: a sponsor, owner and resources 
  2. Set accountabilities and KPIs: establish business case, timelines, governance framework
  3. Deploy cross-functional teams: connect digital development with the front-line users
  4. Have an agile approach: doing all at once will produce waste when sales processes evolve
  5. Enable organizational change: develop skills and mindset in alignment with new systems

    + A bonus: when implementing new systems add an extra element of delight to drive increased adoption.

Need to get started and revitalize your digital sales initiative? We’re happy to help!