The top 10 sales trends in 2020

Dailius Wilson
February 27, 2020

It only seems like yesterday when people were throwing out their “brick” cell phones in exchange for the Blackberry handheld; ushering in a new era of business to business communications. The sales world hasn’t stopped changing since! 

2020 is shaping up to be another large shift and we have partnered with Freshworks to bring you 10 of the top sales trends you need to know to get ahead of the curve this year.

1. Initial meetings secured with gift cards 

Beginning in the middle of 2019; we have seen a substantial rise in the use of incentives to generate appointments in the sales development world. 


In my own tests, I have seen emails with incentives convert at 2.0 to 2.5x on meeting requests generated compared with standard emails; however sales conversation has had no statistically significant change i.e. the % of these meetings converting into paying customers is the same as a regular leads 

I forecast this practice to increase especially as firms build accuracy around their CAC (Cost of Customer Acquisition) metrics or in plain English; they know how much they can afford to pay for new customers and aren’t afraid to spend $$$ upfront. 

As this tactic becomes more common place, I expect diminishing returns from this strategy after July 2020. 

2. Rise of peer based learning 

High profile companies are increasingly looking to their staff to become internal enablers; hosting ongoing workshops & training beyond initial onboarding efforts. 

Although having high performers speak to new and existing staff isn’t a new notion; what is more progressive is the way in which technology is providing a framework for team members to celebrate wins, highlight deal stories and provide feedback outside the CRM. The proliferation of workplace chat environments through tools like Slack, Workplace by Facebook or Atlassian HipChat are providing environments for this to take place.

An interesting academic paper which looks at the impact of peer based learning is Learning from Peers (2014) by Chan, Li which examined a popular cosmetic brand which saw 20%+ increases in sales performance by restricting centralized training and letting peers define the syllabus. 

3. More than 10 evaluators in the B2B Buying Cycle 

I remember writing an article in 2016, commenting on how the average number of evaluators in a business to business transaction had increased to seven. Four years on and now the number has yet again increased - with typical B2B purchases involving 10 decision makers.

The struggle that remains for sales leadership is determining how to coach junior sellers to manage and satiate evaluators whilst correctly determining the correct decision maker. In 2020, expect sales to take a touch longer, especially from outbound movements as teams adjust to interacting with more stakeholders. 

For further information see this release from Gartner 


4. Customer Success as a business partner to sales 

With the cost of acquiring new business increasing; a greater importance is being placed by firms to prevent churn given the cost of retention is typically 20% compared to new business. 

Referrals, cross sales and upsales and increasing managed at a CRO/SVP level - thus we are seeing customer success teams work in tandem or reporting directly to sales leadership. 

Deloitte published a fantastic study which also highlights that of all firms surveyed; more than one third saw a 20%+ increase in revenue when customer success was introduced as a function within their company 


5. Increase in sales operations & enablement roles 

The movement to evangelize sales operations and sales enablement as a best practice is only growing with new role openings and Google search sentiment at all time highs (see image below)

What is yet to be seen in 2020 and beyond is if enablement and operations roles can attract the seat at the boardroom; with Ringcentral a fantastic example of what can happen when this occurs through the work of Sheevaun Thatcher

sales-trends-2020-sales-enablement-search-growth6. Automated data capture and enrichment 

Gone are the days where sales reps need to conduct hours of research before calling a collection of prospects. Modern selling tools in 2020, automatically search for duplicates, add contact & personal information, collect vital company details & present previous deal history making conversations more informed than ever.

The implication for sales in 2020 is that buyers now expect personalization and historical context in all conversations making engagement more difficult for less structured sales organizations

7. Social selling as a long term strategy

LinkedIn went through an evolution in 2013, when the focus shifted from connections & content curation to pure lead generation. This caused executive engagement to decrease as sales teams increasingly used Linkedin as an alternative to email or phone calls to pitch new services. 

In 2020, leading teams are looking at social selling as a long term strategy; similar to how a marketing team looks at brand marketing or retargeting - a mechanism to build passive awareness over time & influence the buyer's journey steadily. 

Companies like or Drift are also centrally managing their corporate LinkedIn strategy through their employees - enabling hundreds of employees to publish key product or customer announcements within a single day. This increases total organic social reach and can build brand equity with existing customers. 

Finally, we have seen the decline of C-level influencers on LinkedIn and the rise of peer based influencers even at the SDR/Account Executive or VP level who are commanding substantial social followings. Brands are realizing that audiences enjoy hearing every day stories from people on their own level and are investing further resources and training to boost the individual profiles of sellers versus attempting to the core LinkedIn presence of a company page. 


8. Moving from point solutions to platforms 

The goal of sales technology in 2020 and beyond should be to keep sales reps from switching between tools as much as possible. The ideology of building an all-in-one solution is manifested in the acquisition patterns of Salesforce (image below) , aggressively adding to it’s already broad offering. 

Sales leaders need to make sure selling time is maximized through tools which are broad in terms of features and integration partnerships which allow account & contact intelligence to filter into executive decision making. 


9. Growth of the remote workforce 

Improvements in virtual conference technology as well as technology powered onboarding & enablement software has fuelled the growth of remote sales teams in 2020. We are also witnessing premier sales talent emigrating to areas outside the main ‘sales territory hubs’ due to improved cost of living benefits. 

Firms which expect a concentrated workforce in one location may be at risk of losing talent in a competitive market. 

Forbes now suggests that close to 50% of American’s are involved in some form of remote work. 

10. Omnichannel selling 

Adding someone into a five step, ten step even 20 step automated sequence hasn’t worked for years; let alone in 2020. 

Multiple techniques are required for success in today’s market with cold calling, live chat, SMS, direct mail, social outreach and in person events mandatory in each sales motion. 

2020 will beckon the modern sales leader to work with marketing, operations and IT to make sure that this experience is seamless and not overwhelming for the customer; a fine and delicate balance. 

Observing any other trends - please let me know in the comments below! 

GetAccept change and simplifies a seller's processes and allows the digital signing of the agreement to take place on the customer's terms with the seller's control. Read more about our product and how you can streamline your sales processes with sales enablement! 

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