Sales Assembly’s Enablement At Work is a monthly collection of tips, trends, and tactics to help you navigate the “always in build mode” world of Sales Enablement – featuring yours truly, Foreman Jeff Rosset, CEO here at Sales Assembly.

Let’s Get To Work!

95% of demos = insert puke emoji here.  Too many demos these days are overly scripted, overly self-serving, and overly unengaging.

That said, I’ve been seeing a trend lately which is based around a totally wild idea of putting the PROSPECT (and their goals) at the center of the demo experience!  So what exactly are these rockstar orgs and reps doing that’s working?

Virtual Discovery
Getting on the phone to ask questions can certainly be helpful, but it’s not efficient, and now you’re asking the prospect to commit to two meetings (discovery call + demo) before they know if your product solves their problem.  That’s frustrating for the prospect.  So, try having a complete list of questions that a prospect can answer via email or a form, instead of a discovery call.  Doing so gets your AE or Pre-Sales consultant all the ammo they need to engage in a very direct and customized demo on the very first call, which kicks the relationship off on the right foot. 

Custom Demos
Speaking of custom, isn’t it fun when the rep spends 90% of the call showing you features you don’t care about!?  Luckily there is a new category that’s bubbled up that allows reps to engage with prospects in an interactive demo scenario that really speaks to their personal needs and use case.  Check out a company like Walnut for some ideas of what I mean.

Effective Follow-up
Following up from the demo 48 hours later, with a link to pricing and the “please let me know what questions I can answer!” is all super lazy.  The best reps take their time, recap the call effectively, offer additional/personalized resources, and really give the prospect a path towards the next step.  Oh, and send the email the same day!


Onboarding new reps virtually can certainly be a challenge, but hiring isn’t stopping.  So here are a few quick tips on how to effectively onboard reps you’ve never shaken hands with:

  • Get new hires interacting with others ASAP – especially leaders.  If they can’t see colleagues face to face, they need MORE interaction than the old days in order to replace that sense of community and belonging to the organization. 
  • Make the boring/easy stuff DIY.  Anything that can be done by themselves should be.  Use the time together to dig into the fun stuff, future state stuff, and strategic stuff.  Get those brains working. 
  • Don’t have it last TOO long.  Onboarding virtually can feel like 2-3X the length of time.
  • Get them learning and developing right away.  Why make someone wait 6 months before you “reward” them with a chance to uplevel their skills?  Show your investment in them (especially when you can’t do things like take them out to lunch or sit at their desk to answer questions), and they will reciprocate with passion and commitment. 

Below are a few tips from leading Tech Sales pros throughout our awesome community:

Jess Ellis, Head of Sales Enablement, Instawork

Q: How do you ensure your company onboarding program is effective in fully ramping new sellers on the team?

A: In my experience designing sales onboarding programs for various organizations, there are many pieces to consider and put into place. However, these 2 components I believe are essential regardless of the company:

  • Constantly Re-inventing & Agile Approach: It is extremely important to be constantly evaluating and pivoting the content that is presented in new hire onboarding to be reflective of what is being prioritized within the business (company objectives, OKRs, future customers, new use cases, etc.) It is easy for an onboarding program to become stale and out of date if this isn’t top of mind.
  • First 90 Day Roadmap: Providing new reps and new sales leaders full clarity as to what is expected at the various checkpoints during the ramp-up period. We then work backward to ensure the items we are discussing in training directly tie to these expectations. Most importantly, they are held accountable to these by their leadership and reinforced through the training and enablement program.


Rich Adams, Sales Enablement Manager, Zoom

Q: How do you ensure sales training really sticks?

A:  Here are a few tips:

  • Focus training on a specific problem/outcome you want to drive home. 
  • Don’t try to boil the ocean in one training and teach them everything. Breaking up training into snippets either in a live format or self-paced/on-demand is great. 
  • Leverage just-in-time learning methods for reinforcement – especially for sales tools and process training.
  • Incorporate activities in training to drive engagement and retention – Use breakout rooms for activities, polling, or tools like Kahoot for knowledge checks.
  • Create a memorable experience, use humor and stories that will stick.

Alicia Babich, Senior Manager, Seller Curriculum & Learner Paths, Pure Storage

Q: How do you ensure sales training really sticks?

A: In my experience, the most important part of the training isn’t the initial concept, collateral, or session itself. Reinforcement matters more, but the most effective reinforcement is actually counterintuitive. Making things stick means:

  • Destigmatizing multiple-choice questions and writing better, more challenging ones.
  • Treating quizzing, reflection questions, and solve-this-problem-scenarios like the learning tools they are.
  • Quizzing multiple times immediately following training, then waiting until some forgetting happens (~a week or two) to quiz again.
  • Connecting old training to new training so learners understand how all the pieces fit together.
  • Creating a culture of self-quizzing so learners are always reassessing what they do and don’t know.

Below are a few interesting stats from Gong as it pertains to your sellers using email during the sales process (The full article can be found here):

  • 2X – The amount win rates increase when emoticons are involved.
  • 15% DECREASE – Success rate when the term “ROI” is used in cold email.
  • 37% – The amount success rate increases when you ask for a SPECIFIC date and time as a follow-up.
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