The role of sales and startup leadership in enterprise deals


As someone who has been both an individual contributor and a leader in the startup enterprise sales world, understanding how and when assisting reps with deals is a big, challenging grey area. 


Should you be on calls… or should you let them handle it? When is the right time to get involved? When is the right time to back off?


You want to help… and it often feels like if you don’t, the deal could go south. 


Full disclosure, I’ve had more instances where leadership involvement has actually hampered my deal rather than helped it… including a few deals lost.


On the flip side, I’ve been fortunate to have some incredible leaders show me how their involvement can be a good thing in the right circumstances too. Including some that have helped me get deals across the finish line, I never could have by myself!


I’m sharing two examples from my own career to help illuminate this.


The first illustrates this delicate partnership done well.


The second showcases where it wasn’t along with things to think about to determine whether your involvement is necessary and in what capacity.


What effective leadership involvement looks like


Figuring out the right level of involvement all comes down to how (and if) you’ll actually add value to the process as a leader. My time with Jacobson is a great example of this done well.


I had been working on a large, highly visible, 7-figure deal with CIGNA for almost a year – knocking on their door, connecting the dots, leveraging other clients like them, keeping close attention to what was happening in their business, nurturing the connections I had within the organization, educating myself on what was happening in the industry, working across multiple buyers, etc. – when FINALLY, I had a breakthrough.


I got the ‘big meeting’ with the key executive decision-maker and his team and flew out solo to diagnose the situation. 


As it turns out, they were in significant pain, under an aggressive deadline, and wrangling a mega backlog that came with potentially hefty fines to boot.  Translating to a potential multi-million dollar, year+ long engagement (service-based solution versus product) was on the table. 


However, there was a significant amount of modeling to be done to make sure we set proper expectations and I had never done something like this before. This is where my boss was the perfect example of helping me break apart a deal to think about it differently and challenging me to do so. 


We built the model and agreement together. And without his support, I would’ve been in deep trouble. I learned a TON and was able to apply that moving forward on future deals.


Why it worked


His involvement was priceless in this situation because he knew the modeling process better than I did and could point out blind spots along with effective solutions. His skills and expertise complemented mine to bring the deal to fruition in a way neither of us could have done individually. 


An added bonus? Much of what I learned from him meant that I wouldn’t need the same level of involvement in the future.


What ineffective leadership looks like


While the leader from my example above did a tremendous job of working with me to collaborate and was instrumental in helping me bring the deal to fruition PLUS delivering the promises made, far too often this is where leadership involvement goes awry.


Too many leaders in my career have gotten involved when there was no real need to do so… and they usually ended up just getting in the way.


Or in the case of one mega-deal with a unicorn startup you’ve definitely heard of, almost derailed it completely.


The deal was humming along smoothly – the head of product, the CS lead, and myself were all over it to make sure we could deliver what we were proposing – and we were setting up a call to go after more budget. 


This is when my revenue leader decided he needed to feel relevant and bulldogged his way onto the next strategy call. But rather than riding along and looking for opportunities to help, his ego took over from the start, leading with “Let me educate you on our business…”


The client called me right after and said verbatim “If he’s involved, the deal is off.”


Key Takeaway


It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.”  – Steve Jobs


If there’s no reason to be in the foreground, don’t be. Work with your team to talk about blind spots and ways you can truly help versus inserting yourself into the equation. Your involvement could do more harm than good, especially if you haven’t done your homework to get up to speed on what’s been done thus far like the story above. 


Joining the call and listening in is fine if your team is ok with it. But let them run point and tap you in if and when needed.


Questions to ask yourself to determine your involvement


Here are a few questions you can ask yourself to assess whether your involvement is necessary and in what context:


  1. Is my ego to be the hero taking over?

  2. What are the desired outcomes?

  3. If the roles were reversed would I want/need help?

  4. If I’m going to jump in, what can I do that hasn’t already been done/worked well/blind spots to get through together?

  5. Has my team explicitly asked for help on something I’m uniquely qualified to assist on?

  6. Could I help them break it apart behind the scenes so they can put it in front of the client instead of me?

  7. Will my involvement undermine my team in any way? 

  8. If I am going to take a more prominent role in the deal, am I fully aware of what my team has done/agreed to/said thus far and on the same page?

  9. How does my involvement move the needle or drag the deal down?


Above and beyond anything else, the best leaders seek to understand first BEFORE they offer up advice or jump in. If our process slows our buyers down, it’s critical to block and tackle internally to remove those barriers versus adding to them.


Things like:


What slows customers down


There is no room for contradictions, perceived incongruences, or inefficiencies on deals of this magnitude. Things must be seamless, consistent, and crisp!


If it’s messy internally, think about what that might look like for your buyers.


Final thoughts


“Bad leaders believe that they have to project control at all times.” – Simon Sinek


In my experience, most of the involvement that makes deals go south starts with the wrong expectations from the top down. 


As a general rule, trust your team to run point, work with them behind the scenes on what they need, block and tackle internally, and participate in meetings when you can help the process not hurt it.


Lastly, if you are going to be front and center with the client, do your homework to ensure you all are on the same page. 


According to Biznology, 82% of B2B decision-makers think salespeople are unprepared as it is. So ensure you’re not adding to this perception. Nothing puts doubt in an enterprise buyer’s mind like inconsistency and sloppiness!