Enterprise Sales... from the inside

A clothing sales rack. Nothing like selling in to the enterprise market.
Photo by Artem Beliaikin / Unsplash

When you spend nearly 25 years of your career working for large corporations, well, you've seen a few things. Many of which you might wish you hadn't, but nonetheless, taught you a lot of important life lessons. And a few unimportant ones. What is often a challenge for people who don't work in these environments, is to understand exactly what goes on behind the security badge locked doors.

Many questions are asked:

  • How, exactly, do you spend 7 hours in meetings every day?
  • You had how many bosses in the last 2 years? Double-digits? That's a record.
  • Wait, and you have how many bosses right now?
  • They spent how much money on that?

Look, it isn't always glamorous, no matter what brand name is on your badge. Sometimes it's just as dirty as it is washing cars for a living (which is how I started my career, but that's a story for another day). One of the ways it's the toughest is picking out a new vendor to replace one you're not happy with. Often times, the outgoing vendor is blissfully unaware that things are bad. They love their product, its the best, and all our clients do, too... until they all depart for greener pastures, which invariably turn out to have just as many flies as the pasture they left.

Trying to explain how that process works to people who have never seen it from the inside can be a bit of a challenge. They never can quite believe that the company isn't stringing them along; that there is always something they're not being told. While that is always the case, what isn't being said, is never what you'd expect.

I recently undertook the endeavor to try and explain how this goes down to some colleagues. What you'll see below isn't a real situation, but the pieces of it all happened at some point in my career, across several very large organizations. I know, you're thinking, why on earth would you want to read about organizational politics, but I did my best to make it entertaining for all, so I hope you give it a chance. Without further adieu, here is...

Enterprise Sales...

from the enterprise side

(Assume the existing contract terminates on December 31, 2025.)

18 months out (July 2024)

  • The company begins discussing future of the agreement and decides to look at moving to a new partner due to under performance of the existing partnership.
  • Capital budgeting cycle starts late summer, so company staff begin laying out process to put out a request for proposals (RFP), budget estimates, & timelines to implement a new partnership.

15 months out (October 2024)

  • Key stakeholders are brought in to validate the planning effort, key improvements needed, and strategic alignment.
  • The local market team puts out a request to other business units & international markets to see which solutions are in use, which are good, which are not, and why. The market may quietly ask former colleagues who now work in other companies what they are using and why.

12 months out (January 2025)

  • The company aligns on short list of potential partners and begins making contacts to let the partners know that an RFP is coming, and what the scope of the effort will be.
  • Partners begin onsite visits to understand what is and isn’t working today.

9 months out (April 2025)

  • The company wakes up in a panic, realizing they likely won’t be able to get the work done before the current contract with the legacy partner ends. The company decides to cut the partner list to two candidates, neither of which have worked with the company previously, but the architect's nephew knows the janitor at one of the partners and swears by the conference room leftovers they serve their onsite visits. The other potential candidate partner is someone that an executive worked with at their prior company. Everyone in charge of implementation is at a loss for exactly how these are the two 'best' companies, but they vow to get it done, if only they can start now. They just know they can make it in time.
  • Both potential partners are brought in on short notice to pitch to department heads, and maybe other select leaders. Fancy dinner invites go out for the nicest restaurants in town. The wine flows and everyone feels great anticipation for such a promising new world, with a partner who actually knows what they're doing.

6 months out (July 2025) 

  • The company awards the business and begins contract negotiation, in parallel with implementation process. No one inside the company who is tasked with the work is clear why this partner; it doesn't even meet the core requirements that the outgoing partner is capable of doing. The selected partner is asked to do their part of the work on credit, as the company will pay all bills once agreement is signed. I'm sure that will only be a couple weeks from now. Trust us; we've done this a lot.
  • Technology & operations teams, supported by Marketing & Finance, start to scope project. Immediate conversations around how to cut scope begin, so that there isn’t a gap in service, as no way the full feature set can be implemented by end of year.
  • The company also presents a gap list that must be filled before they could consider going live. Partner is told to get it done or the deal is off.
  • The company global leadership hears about the year old project for the first time. Leadership tries to get the partner to extend service to the rest of the world, but at a lower price. Contract negotiations grind to a standstill.
  • Everyone agrees to break the scope out into phases, with the full implementation now not complete until mid-year 2026. The company admits they can’t get their work ready by end of year, and admits to the departments there will be a gap in coverage until sometime Q2 2026, with the rest of the features coming “soon after”.

3 months out (October 2025)

  • Security functions find out about the project and are brought into the conversation for the first time. Gaps found in data privacy and security are identified, with security refusing to sign-off until requirements are met. The company threatens the security team to just do it anyway, as their coverage gap is already too large and the department heads are threatening to revolt and pull funding.
  • With the holidays fast approaching, everyone is working furiously, with the go-live still set at January 1, which everyone knows is impossible at this point, but no one is willing to admit.
  • Contract is still not signed, having sat on an executive's desk for over a month, untouched. Currently it's stuck in the hands of legal at headquarters, who are arguing over whose paper this should be on. Partner is asked to continue in good faith. The company agrees to pay Q3 bills in Q4, even without an agreement, with the understanding that they must be repaid to the company if the implementation never goes live.
  • The outgoing partner is finally informed of non-renewal, but asked to go month to month to “ease the transition period”. The company calls up contract provision that legacy partner must export all data. New partner informed they need to import 5 years of historic data before go-live can happen.

1 month out (December 2025)

  • Division president calls the vendor with the business lead and the CTO. Can we work the holidays to get it done? Even with that, no one is confident in going live. Date pushed to February 1, which everyone knows is also unreasonable, but no one wants to admit.
  • Contract nears completion, but now caught up on if the company logo can be used on the partner website or not.
  • The company completes their data feeds three days before the holidays. Tells partner they need a plan to make go-live on January 1. Partner admits they cannot meet that timeline.

Planned Cutover (January 2026)

  • Legacy vendor misconfigures the company's account and shuts off service inadvertently. The company doesn’t notice for 2 weeks and is livid once they find out. Proceedings to penalize legacy vendor for failing to meet SLAs are threatened if service isn't restored immediately and credit for missed service levels are not issued.
  • New partner continues to work thru gap remediation and configuration.
  • Needless to say, the go-live date blew past everyone like a supersonic jet.

Cutover +1 (February 2026)

  • The new parter completes configuration and gap remediation. The company is in the middle of a massive marketing push to overhaul their product line; requests 6 week delay to mid-March due to operational complexities.
  • Charlie Brown lays in the dirt, wondering exactly how he could have missed the football one more time.

Cutover +2 (March 2026)

  • First phase finally live. Parter spends the following 6 weeks working with the company to resolve integration issues not tested due to volume of data.

3 month live checkpoint (June 2026)

  • Company leadership is dissatisfied with first release and don’t understand why this didn’t fix all the company issues, from product quality, speed to market, and labor costs, immediately upon go-live. Company and partner leaders meet to talk thru a new campaign to build adoption of the service.
  • The company begins discussing future of the agreement and decides to look at moving to a new partner due to under performance of existing partnership, which ends in 18 months.