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Five keys to effective sales readiness in 2021

In 2020, hundreds of sales organizations rapidly and abruptly shifted to virtual sales training methods primarily due to the force of circumstances. In 2021, however, remote work is no longer an unwelcome interruption to business but now has become the new normal.

According to Gartner, for instance, CSOs expect 58% of the sales force to remain operating virtually by the end of 2021 as against 24% pre-pandemic. Further, over a third of CSOs are permanently transitioning some or all of field reps to virtual sales, and another third is considering doing so.1 Unfortunately, Gartner Research also shows that 57% of CSOs feel their sales teams are underprepared or only partially prepared to deliver the same level of value in virtual versus in-person engagements.2 This implies that organizations need a major shift in how they structure their sales readiness initiatives in 2021.

Here are five principles for restructuring your sales readiness program to ensure that your reps are ready to go out and start selling in this changed environment:

  • Update strategy and playbooks for omnichannel selling:

As McKinsey research shows, omnichannel buyer journeys are here to stay with buyers preferring a combination of in-person, remote, and digital self-serve interactions with sellers in equal measure.3 The report notes that omnichannel is not simply a trend, nor a pandemic workaround, but a critically important fixture for B2B sales globally.

Sales organizations cannot respond to this decisive shift by simply implementing existing strategies via digital channels. Instead, companies must fundamentally rethink questions such as how to avoid channel conflict, provide the human touch in remote interactions, and offer customers a tangible product experience in the absence of physical demos and walkthroughs. Only when these new sales playbooks are written can reps be adequately trained and readied to sell in the new normal.

  • Make learning more contextual:

One of the key advantages of virtual sales training processes is the ability to integrate training with the sales workflow. Such contextual sales guidance ensures that sales reps are motivated to consume sales training content that is highly relevant to the most immediate sales tasks. Information is provided as short, interactive, and easily digestible pieces of content focused on specific learning outcomes that the learner can easily consume. Such a process of microlearning also helps organizations deliver the necessary domain and skills knowledge to sales teams remotely at a time when sales kick-offs and product launches are unavailable as in-person sales training events.

  • Use gamification and collaboration channels to replace the office environment:

Lacking the immersive office environment, remote sales teams are likely to face challenges with regard to motivation and innovation. Gamifying sales readiness, with techniques such as badges, challenges, and leaderboards encourages the innately competitive nature of sales reps and pushes them to engage more enthusiastically with sales training and other activities. At the same time, it’s also important to provide forums or virtual channels in which reps can engage actively with other team members. This allows them to learn collaboratively from each other, drawing on the collective experience of the sales team.

  • Support experiential learning:

Reps can’t learn everything they need simply by reading or watching demo videos. Some of the most crucial skills can only be gathered through experiential learning, which is learning through actual practice. Modern sales readiness platforms make recording and distributing demos and role-plays on video easier than ever. Sales organizations can start by creating short, highly context-specific examples of the crucial skills required in cold calling, elevator pitches, objection-handling, and so on; then, get reps to record and share their own practice pitches to get coaching on how to enhance those skills before speaking to customers. The best pitches can also serve as content assets for training new cohorts of sales reps.

Pitch analysis is one of the cornerstones of an effective sales readiness program.
Ongoing pitch analyses by managers ensure that sales reps are sales-ready at all times in an ever-changing market environment.

  • Use AI and analytics to provide evidence-driven training and coaching:

AI-enabled sales readiness platforms can track sales training progress beyond mere consumption metrics. In particular, such platforms can analyze at scale the quality of practice pitches based on factors such as topic coverage, delivery, mood, and keyword usage, and, thereby, identify which sales reps are ready to pitch to prospects and which reps require more coaching and training. This overcomes the most common factors faced by managers that lead to coaching failures, namely, lack of time, manager bias, and poor identification of areas of improvement. Furthermore, these platforms can be integrated with the CRM software to monitor real-world sales performance, identify pipeline leaks, and optimize sales training and coaching processes.


In a digital-first world, sales organizations can’t wait for sporadic in-person sales training events to update reps’ knowledge and optimize sales skills. Sales readiness can’t wait for the next quarter or the following year. It must begin now and become a core capability of every sales organization. For rolling out an effective sales readiness program, organizations need to update their sales playbook for omnichannel selling, customize sales training for different sales personas, make learning more contextual, support experiential learning, and use AI to provide analytics at scale.