We Ran Our Company’s First Sales Hackoff

From “Ideation” to “Presentation” and finally (hopefully) “Creation”

In my last blog post we talked about how a group of young future sales leaders participated in a bookclub on a biweekly basis to curate ideas that would shape the company’s future.

Since then I have spent endless hours working independently with them, taking their ideas and coaching them on how to properly build a business case. They then had the opportunity to pitch it Dragon’s Den / Shark Tank style at our Sales Hackoff to our C-Level executives.

Needless to say the expectations of the executive team were low with a bunch of junior sales representatives but they were blown away by the breadth and depth of what we provided. On top of that they were given visibility on what type of talent their company was developing.

I’m here to share with you how we did it and how to get your Hackoff to be as successful as ours was.

“Ideation” to “Presentation”

A. Foundation

For the first Hackoff, we framed it around the theme of our first bookclub review on the “Sales Acceleration Formula”. Many weeks of preparation were done in advance and more information on that can be found in my last post (below). This creates a focus on key concepts that will help a growing sales team take the next step in its growth.

B. Support from Executive Team as Judges

Compared to traditional Hackoffs where developers are presenting their days work to the company — the purpose of this was meant to be a presentation for executives to understand what the Sales Team needed to scale and grow.

This required a 2 hour time-block where our CEO, CCO, and CTO could participate in something completely experimental. As judges, they were scoring and providing feedback on the following things:

  1. Idea and Impact
  2. Research
  3. Viability / Scalability
  4. KPIs
  5. Execution Plan
  6. Presentation

C. External Channel Support

As the manager you should reach out to the other channels and departments and work to remove barriers for your team. Research was a key component in our Hackoff and I made it aware to all the relevant departments in my company (Marketing, Product and Support) that my team was working on this Hackoff.

It can be confusing / concerning to have a sales representative walk up to your department asking for information that deals with their department, so setting the precedence of what this is for and the potential impact it provided really helped ease a number of concerns for those involved.

D. Business Case Preparation

Some of your sales team members may be creating a business case for the first time in their careers. Setting them up for success means presenting to them the format and expectations of the Hackoff and then spending time with them afterwards in developing their business case acumen.

Focusing on why this is an important skill for them to have in their careers will go far in keeping everyone engaged (note: this has been the most time consuming but rewarding exercise as you are seeing your reps grow before your eyes).

The format of our business cases were the following:

  1. What is the Idea?:
     — What are you trying to accomplish?
     — Can you articulate what the problem is that you’re trying to solve?
  2. Why You’ve Chosen This Idea:
     — Research (Internal / External, Qualitative / Quantitative)
     — Impact for your company (tie with short-term/long term strategy)
     — Impact for your Sales team (revenue / operations)
  3. How Are You Going to Do This? — Execution Plan
     — Timelines
     — Who is involved?
  4. Cost & ROI
     — Time / Resources
     — Sensitivity Analysis
  5. What is Successful?
     — KPIs to strive for
  6. Next Steps: What Is Your Ask?
     — Call to Action

You can see how this aligns with how the judges were scoring.


  • Start early: its in the nature of a sales team to wait until the last minute. Make sure you’re establishing with them clear deadlines and deliverable dates with them.
  • Focus on the question of: “What problem are we trying to solve?”
  • Gear the presentation to the executives: What are they thinking about in long term strategy, how does what you’re working on apply and help?
  • Encourage reps to provide customer stories. These should be mentioned at the beginning and tied in at the end of the presentation.

E. Practice, Practice, Practice!

Salespeople are supposed to be good at presenting but there is always room for improvement. I recommend having your team practice amongst themselves and then dive into 2 separate sessions with them (one before the big day) to give feedback.

Managers review the deck (are the slides too word heavy? crowded?) and overall presentation style to ensure there’s uniformity in what’s delivered to the judges.

The Day of the Pitch

Book a large enough room and set up in a Dragon’s Den/Shark Tank style format. The team should have 10 mins for presentation with 5 mins Q&A afterwards. Open the event with the executives to remind them of their roles in the Hackoff. One thing that I did not do was provide them with a scorecard (whoops!) so that is highly recommended.

Also, open up invitations to anyone who would be interested or benefit from the hackoff as well to attend in the audience. We had Business Development and Support included for visibility as some of the Hackoff’s ideas pertained to them.

Your team may be nervous or edgy, keep spirits up as it may be a nerve wracking experience. They’ll thank you for being the calm presence in the end.

Post-Sales Hackoff

After all the presentations are done book off 10–15 minutes to receive feedback from the executives. For us, it was a great opportunity to recap on what went well and what we needed to improve on.

For the Hackoff ideas we decided to break the ideas into two sections: (1) those we can execute immediately and (2) what needed more details to re-apply for further approval to execute.

I took the recap and provided 1:1 coaching with each rep. For those that needed more details, it was more due to the fact that their ideas were more intricate but had big potential impact. They were successful in drawing attention but required the sales rep to get deeper into the weeds.

From “Presentation” to “Creation”

We’re now in the executing phase of many hackoff ideas. I’m extremely proud of my team for all of their hard work and growth during this time.

Each individual realized something about themselves that they’ve never seen before and it shakes things up for a bunch of millennials who always want to know the big picture.

It also provides a stage for you to really show off what your team can accomplish with open minds, a learning/experimenting culture and structure for success. This is the kind of team your executive team will safely believe in and continue to invest in their growth and future.