Dan Bodoff

Enterprise AE & player-coach|Building the agents and workflows behind my own pipeline|SaaS, security & AI products

Work History

Before 2014
  • Maine Digital Press, owner
  • National media buyer, 11 years
  • Classical music / jazz performance major

AI Fluency Journey

Specifically focused on supporting sales craft.

Personal Case Studies

Complex deal management

Selling internally as hard as externally

Outcome

  • Closed won; largest deal of my new-hire group
  • Business case and org chart notes were used for internal selling to the CEO
  • CEO approved 2 of 3 requests from the customer's legal team
  • Strong multi-champion and business development ensured post-sale success

What I learned

  • Champion development and testing are equally important
  • Business case development starts early, and is just as important for internal selling as external selling
  • Even an early, rudimentary understanding of a customer's org chart can surface areas of opportunity

How my process changed

  • Every account I work begins with an org chart
    • Developed skills and agents to ensure initial development, and constant growth and pruning
  • Business case development can start even before an initial customer meeting, and it can demonstrate meaningful understanding to a customer
    • Developed skills and agents to ensure this happens based on research and learnings as engagements progress
  • Pre-discovery discovery became a key part of my process

A national communications company had tried to buy the platform several times. Every attempt died the same way: no one would own the budget, and my own company's legal team would not accept their terms. When the account was assigned to me, much of its CRM history had been lost, and I was unaware of the tense history, leaving me to work twice as hard to determine the best path to a win.

New VP initiative reports here IT owns total budget · signs contract Business unit Aowns a shareKPIs mapped · initials Business unit Bowns a shareKPIs mapped · initials Business unit Cowns a shareKPIs mapped · initials Business unit Downs a shareKPIs mapped · initials Champion weekly tested Dashed: champion's internal influence and introductions

Cross-functional partnership

Managing product as carefully as the customer

One of our largest and longest-standing customers was very interested in purchasing our newest product, a platform for which we had yet to identify product-market fit. Unfortunately, their environment exceeded the current capabilities of the platform, and two roadmap items needed to land in order to align with their year-end initiatives. I brought the product's Head to a customer conversation, and, thrilled by the potential alignment, they promised to deliver the roadmap items within four weeks. Unfortunately, product did not have the ability to deliver this in that time frame.

The impact of the promise

  • The cross-functional evaluation team used the promise to rally other IT groups.
  • A miss would not only cost them credibility internally, it jeopardized their ability to hit their year-end goals.
  • We all carried the same concern that our relationship with the customer would not be the same after a miss like this.

How we resolved this

Internally

  • Raised the concern with the Head of Product, not in front of the customer
  • Coached Product on running these conversations: two-thirds on the customer's goals and outcomes, one-third on where the product fits and where it falls short, limitations stated up front
  • Identified the actual possible timeline for delivery, and what was required in order to bring roadmap features forward
  • Revisited the calls and our notes to identify two additional ways we could impact year-end KPIs in the short term

Externally

  • Explained that there were issues with the timeline commitment, asking for a live call to discuss
  • Addressed the problems empathetically, and directly
  • Proposed a near-immediate proof of concept based on current availability, and how that would impact year-end KPIs

What we changed going forward

  1. Pre-call alignment with productBefore any joint customer call, agree on what is confirmed, what is tentative, and what still needs validation. Conversations run two-thirds on the customer's goals, one-third on where the product fits and where it falls short, limitations stated up front.
  2. Shipped capability before roadmapWhat already works first, aligned to goals. Roadmap is additive when meaningful.
  3. Leverage proof of concept for momentum and validationStructure proof of concept around proving specific outcomes, with commercial terms and approvals settled before the POC begins.
Where it ended. Proof of concept agreed, commercial terms and approval path in place, legal review passed, kickoff scheduled. Then a layoff ended my involvement. However, the result I can stand behind is taking a customer from a broken promise to a signed-off evaluation with a clear path to purchase.