Scaling B2B Sales

Rubicon Breakfast Roundtable #1 Scaling B2B Sales Notes

With the end of 2017 approaching and with 18 months of hosting almost weekly events, I took some time to reflect on all of the events that I hosted and those that I attended. Pretty quickly I realized that I enjoyed and learned the most from small and curated events about very specific verticals or issues that stimulated discussion in an open and honest way, which meant that those events were behind closed doors 99% of the time.

Having attended some great discussions, I wanted to create a series of regular events for early stage founders in NYC that would bring founders and experienced industry leaders together over breakfast. Through countless coffee meetings and discussions, I realized that many early stage founders go through similar growing pains even when they are in different verticals or going after different market segments, yet they often don’t have a platform to share and learn from other founders “at scale” (i.e. not in one-on-one coffee or drink meetings).

After some brainstorming, I went out to create an environment to bring seasoned executives from leading Fortune 1000 companies in NYC to lead discussions about specific issues. Each discussion is centered around a particular topic and each session is led by two industry experts. The first event was focused on Scaling Sales and the upcoming session is focused on B2B Hiring and Compensation.

Big thanks to Randy Adler and Fox Rothschild for hosting us at their offices.

I will try to post notes from each of the roundtables monthly to share the key takeaways. Notes don’t do justice to the discussion, but I will try my best. If you’re in NYC and are interested in attending or leading one of these discussions, shoot me an email.


Pre-meeting & Initial Conversations

  • Identify the key decision makers and get into their mindset to understand their needs and find product/market fit first
  • Figure out where the fit for your product is in the company and what problem the product is solving for that client specifically
  • Map out how the product affects and flows through the potential client
  • Profile the buyers and decision makers and the power dynamics inside the organization
  • Customize a pitch for each person in the buyer room
  • Speak to people from other departments to demonstrate confluence of interests and demonstrate use cases from multiple angles
  • Think about how to keep the people that can say no out of the room during pitches and negotiations
  • Find the person who believes that innovation is a career maker, not a career breaker and has the interest and proclivity to bring in innovative solutions


  • Define pilot success criteria early and control the pilot ecosystem
  • Control the scope of the pilot – the larger the scope of the pilot, the higher the chances of issues surfacing and thus failure
  • Manage communication plans for feature requests and issues proactively during pilots
  • Arm internal sponsors and champions proactively with all the information needed to get approval for next phase
  • Do internal demo days for other stakeholders in the company during the pilot, get them to buy into the vision
  • Be the PM of the pilot, don’t rely on the client’s own PM

Contract Negotiations

  • Throttle the initial contract value to get a pilot or small deal done quickly to keep it under procurement signoff level
  • Offer free pilots if need be, if you can’t sell a free pilot then you probably shouldn’t be in business
  • Create language for an easy out, but figure out how to roll pilots into deployments
  • Figure out how to sign contract and play with financing terms to get it done, once in the enterprise, much easier to expand as an existing vendor
  • Manage procurement + legal proactively during negotiations
    • Don’t give away big discounts if can’t get something in return (references, logo on website etc)
    • Get business owners to put pressure on procurement + legal, few people want to be seen as an obstructionist and holding the company back
    • Figure out what 10% of legal terms you actually care about changing and focus on that, keep edits light
    • Investigate if target customer has own MSA/legal department
    • Own MSAs indicate seriousness, if you have time, start with your own paper
    • Sign a shorter contract – survive and advance – get the ball rolling and try to renegotiate once they are using it and see the value
    • Aim for an LOI before contract to make progress more definite, even if LOI is not binding


  • Need to show progression with clients, if it takes too long with certain clients, move on to others
  • Marinate the pipeline, the longer the sales cycle, the bigger the pipeline has to be
  • Pipeline management is as important as revenue tracking

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