Break Tradition: How to Reform Your Sales Strategy and Give Buyers What They Actually Want (Peter Ostrow of Forrester)

By Tom Pisello | September 15, 2021

Recommendations for Evolving Your Sales, Content and Value Enablement for 2021 and Beyond

More decision maker stakeholders, more buyer interactions to support, and constrained customer spending … Despite there being more sales opportunities this year, selling is indeed more difficult in 2021.

To kickoff our Evolve 2021 community and customer event, I had the pleasure of interviewing Peter Ostrow, VP and Research Director of Sales Enablement Strategies for Forrester, to discuss current sales enablement trends, and dig into some important new research.

First, we discussed the challenges that sellers report, and how these have changed pre- and post-pandemic.

The top seller reported challenge: “How long it is taking for buyers to make a decision”, up 20% over the past two years to take the top spot. More scrutiny is being paid to each purchase decision, and buyers remain risk averse, taking longer to make decisions by having to overcome more approval hurdles and procurement process steps.

One of the key reasons for the lengthening of decisions, sellers continue to be challenged by purchase-by-committee, with more stakeholders involved in specifying, reviewing, and scrutinizing each decision. Each decision maker has their own unique perspective on the challenges to address, outcomes to achieve and risk tolerance, making it more difficult to get everyone up to speed, on-board and gain approval consensus. No wonder more deals are delayed, or flat-out ending in “no decision”

Of surprise, sellers do report a challenge with virtual selling post pandemic, but not as much as one might think, landing at the number three spot of top sales challenges. Sellers did highlight the difficulty selling in an environment where salespeople can’t meet the buyers and customers in person, as many long for the days of in-person meetings to better workshop and collaborate, the breaking of bread to gain rapport, and a handshake to close the deal. Forrester research said that although 40% of sellers say how much easier it is to conduct meetings with customers, 55% of sellers are say that the inability to meet buyers and customers in person is directly hurting the ability to meet quota.

For developing a go forward Sales Enablement strategy to overcome these challenges, Peter mentioned how important it is to take these top three challenges head-on as a priority over the next twelve months:

1. Length of the decision cycle – It is recommended to enable sellers with an understanding of what a buyer typically needs at each stage of the buying journey, and content sellers can share with the buying committee to proactively facilitate and accelerate the decision cycle.

For example, if you know a buyer will put together an RFP, you should have an evaluation framework and competitive guide. If you know you must go through a security review, you can pre-package all the security documentation, anticipate and share with the buyer before the security compliance team must ask for the information.

And sharing this content with the buying committee in a collaborative “buying hub” places all the decision-making content in one easy to use and leverage location – all with tracking so you can assure consumption, leverage and engagement of all the content provided.

2. More stakeholders – It is important to empower sellers with conversation guides, content and training / coaching to help understand the unique perspective of each stakeholder, align use cases and articulate potential value and outcomes.

3. Virtual selling persistence – with a return to in-person meetings remaining elusive, it is vital to get virtual selling skills further improved. Although most sellers have upped their virtual game, many have sub-par on-screen presence, and lack the orchestration, discovery and follow-up to take digital engagements to the next level.

Providing interactive presentations, dynamic content and improved sharing tools to fuel on-line engagements, and role-play training, coaching and feedback to optimize engagements you can better enable sellers and drive more inspiring and impactful interactions.

Are Your Ready for Even More Interactions?

During the decision-making process, a more active, cautious and larger committee of buyers are driving more interactions with selling organizations in each and every deal.

Two years ago, buyers would interact with a selling organization just over 17 times from first engagement through decision, with 53% of the interactions self-service.

Fast forward to today and we see a dramatic 54% increase in the number of interactions, now just shy of 27 touch points per decision cycle. And these interactions remain almost evenly split between self-guided interactions (55%) versus sales driven and personal interactions.

The question for any selling organization needs to be: How do we up our interaction game to maximize every engagement, inspire decision making and differentiate?

1. We find that interactions can be better fueled by rethinking content, to be more personalized and dynamic. For example: Converting traditional PDFs and large presentation decks to make them more animated, to capture attention, and providing menus and hotspots for navigation and drill downs, facilitating hierarchical and create-your-own-journey navigation.

2. The commercial teams can optimize personal interactions, working to improve seller engagements in meetings, and follow-ups post meeting. Fuel engagements with content that is animated, dynamic and supports create-your-own-journey navigation for quick pivots to just what the buyer cares about. Deliver workspaces and intelligent content recommendations to sellers in order to guide them to just the right content for each selling situation. And make sharing easy, empowering sellers to create their own workspaces to share with customers – buying hubs to contain all the information the buyer needs to educate and gain consensus amongst all the decision stakeholders and make a purchase decision easier (all with complete visibility into consumption).

Sales Enablement Priorities

To wrap up our session with Peter, we reviewed the priorities sales enablement leaders indicated were top on their list, to learn what these leaders planned on focusing on for the next year.

To no surprise, to help transform the selling capabilities and commercial teams, sales technology has been the focus and a top priority, with investments to get the most productivity and effectiveness out of sellers, and to make sure that sellers know how to leverage the new tools and the investments don’t go to waste.

The top three priorities for sales enablement include:

1. Deploying and training on new sales technology – helping sellers to clearly understand why new technology is so important, how to apply the new technology to improve their productivity and customer engagements, and how to be capable, credible and confident in leveraging the tools in their day to day.

2. Improving rep use of social media – prospecting via trade shows and conferences will remain constrained, so sellers are replacing and supplementing their opportunity creation with social media. Sales Enablement is helping improves sellers use of social media to assure it is being used in a value-added fashion and is successful in building connections and opportunities.

3. Creating and restructuring the sales enablement function – As sales enablement advances, where it reports and who it supports has evolved. Many sales enablement functions are quickly expanding to accommodate all of commercial team versus just sellers, especially customer success, support, professional services and more. These teams require their own workspace portals, content, learning and readiness, expanding the function dramatically, and providing even more pressure to getting enablement evolving and right.

The Bottom-Line

Throughout the interview with Peter Ostrow, I was able to step back and gain perspective on just how customers, sales skill requirements and enablement scope were all evolving, and how important the sales, content and value enablement roles are in helping to address and overcome new challenges.

Maintaining curiosity and a growth mindset will be key as the challenges, responsibilities and potential solutions advance, making it more important than ever to be an EVOLVER!

Checkout the On-Demand interview with Peter Ostrow of Forrester here:

Checkout the original presentation supporting the interview here:

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