Blog
"frustrated salesperson"

Keeping Your Salespeople Engaged During Long Sales Cycles

Having worked in enterprise sales for years, I’ve learned a lot about handling long sales cycles and the unpredictability that comes with larger deals. With that said, here’s the common challenges that I have experienced, and my words of wisdom keeping your salespeople engaged during these long, difficult deals.

Common Challenges Salespeople Face

  1. Strategic projects move slow, VERY slow, and appear and disappear at a blink of an eye. You have to anticipate change and be ready to be flexible for your customers’ ever changing business.
  2. The only constant is change. Re-organization and shifting priorities – a sales rep’s nightmare – become a normality when selling to large enterprises.
  3. There is always stakeholders you aren’t aware of and typically a lot of them. One enterprise project I am currently working on told us they have over 100 corporate stakeholders involved in our project’s success – not counting the end users! That’s a lot to navigate for 1 rep.

Challenges Faced by Sales Enablement Leaders

  1. How do we help enable sales for projects to move quickly and efficiently before the deal window closes?
  2. As reorganizations happens within both your own sales organization and your customers’ – how do you keep track of the sales interactions, contacts, and keep a pulse on business owners who may leave your project, but be a valuable contact for your company down the line?
  3. How do we help sellers keep track of all of the stakeholders and ensure we get these stakeholders the right materials, collateral, information, references at the right stage of the sales cycle?

Sticking of the rule of three today, I have 3 words for you. IT’S NOT EASY.

My Words of Wisdom

Here are some ideas you can start to think about internally as you look to refine your Sales Enablement strategy to accommodate larger deals.

  1. Often times projects go stale because there is no budget available or a competing project with similar or higher priority. Sales Enablement software can help by equipping your sales team with relevant sales content early in the sales cycle that can demonstrate potential project ROI, benefits, and results from other customers. This all helps to build your champions early – before the RFP starts and procurement shuts the door on you with the “silent period.”

    If you can enable your salespeople to arm your prospects with content relevant to their project early and before the competition, it will help ensure (your company name here) is in the driver seat when an RFP launches or when a dead project resurfaces.

  2. When a $1m deals turns into a pilot, or a marketing project becomes a Sales Ops project, your salespeople need to be equipped with the right information to service this new business unit. This may mean new presentations or demos with a whole new spin on them – all while not losing track of your previous contacts, interactions, etc. This also requires recording information into your CRM, marketing to these stakeholders over time, and record keeping in case account changes happens within your own sale organization.

    Modern Sales Enablement platforms like Bigtincan can allow you to program your CRM system to automatically recommend new information when buying stages change, the business unit involved changes, or new stakeholder personas are introduced to your sales cycles.

  3. Organizing and suggesting content to your salespeople based on buyer persona can be a very valuable asset to ensure you are getting to as many of your buying stakeholders as possible, and winning them over by getting them the right information to meet their needs – faster and better than your competition – building confidence and votes over time.

In summary, Sales Enablement software can help your sales reps, existing customers, and prospects stay in touch, be optimally informed, and help everyone stay flexible over the course of long decision making cycles.


Help your salespeople automate the persistence that is needed to be successful in big accounts and replicate what your most tenacious reps might already be doing naturally. Get a demo of Bigtincan today!