Ep. 2 : Founders must sell and that makes me sad.
A technologist/founder's take on learning to sell
In this episode:
Time to rethink the proposal. Or is it?
I confront the idea of “Buyer Enablement”
Sneak peek at our “Backdrop” concept
Tools I’m trying this week (ROI Calculator?)
Is this thing on? Guess so!
Thanks for all the positivity from our launch of the Closed/Lost email. Our stats were pretty positive - sharing below. 48% open rate is great but please tell me what I can do better. What else do you want to know from a founder’s perspective?
Selling software into organizations is terrible! It’s the absolute worst. It’s hard, sticky and just an all around slog.
Some background — My last two startups sold enterprise software into mid to larger organizations (read BigCo) and we learned firsthand how difficult it is to get deals to close with any sort of predictability in any reasonable timeframe. Sometimes it was slowed down due to IT, other times due to compliance questions, and many times it just outright died when other departments got involved.
Overall, there were too many hands in the cookie jar and nobody was happy.
And, we weren’t alone — we’d deliver a great pitch, followup with an awesome proposal and yet still get ghosted or politely told to buzz off.
We used some pretty legit software (PandaDoc, we see you) but ultimately couldn’t satisfy our account.
Make Proposals Great Again.
We spent our lives putting together proposals. Not even joking - 2am mornings were commonplace to get a proposal back to WidgetCorp. And why wouldn’t we — our first interaction would be an amazing demo with an engaged VP of something who saw value and the pain we solved. They wanted to solve it, they had the budget - what could go wrong?
But, no matter how much time was spent on a proposal, it always seemed to miss the right people. Our influencer might be perfectly content with our proposal but IT needed another set of answers, Marketing needed to buy in (requiring yet another demo), the GM needed validation before budget was spent and another business unit recommended a POC before moving forward. All the while, A CXO wanted background on our company and case studies relevant to their industry and finally the actual users who would use the product needed to be wooed and know how it would help their daily life through video since our customer VP woudn’t jam it down their throat for fear of low adoption or a full scale prison riot.
It was a complete and utter mess and nobody walked away satisfied. (there’s a joke here)
Gartner nailed it with this diagram —
77% of B2B buyers rated their purchase experience as extremely complex or difficult.
Back to our crappy proposal - how are we going to serve different roles and actions in the same document? Not going to happen.
Too many groups, not enough focus
Sales. IT. Marketing. Finance. Oh my.
Yep, we’ve had to deal with them all, and chances are if you’re in software sales you have as well. It’s not getting better.
Sales is buying it but ultimately Marketing will load the content. Ok, let’s talk to Marketing. Marketing is in, but doesn’t want to share budget. The GM needs a demo and there is another business unit in Asia that has a similar solution. Pause while we find out what’s going on there. And then IT. Oh IT, you cruel soul crushing demon.
(but, in all fairness IT has a point. Software is getting out of control in the organization — Shadow IT is on the rise and its becoming harder for IT to standardize approval processes causing stakeholders to just “beg for forgiveness instead of ask for permission”. <3 you IT mwah. )
The only thing that makes this process worse is when it goes on so long you have turnover in your customer org. Now greg replaced Julie and Karen is acting blah blah blah. Rinse, repeat. Actually, more like Closed/Lost.
Ultimately there was no focus standardized across departments so balls were constantly being dropped. Many times our customer just threw his hands up, succumbing to the slow death that is complacency.
Pitstops kill the road trip
Back to our story — Karen in Marketing needs a demo, Steve in Ops needs references and our influencer in sales just needs a quote. If you haven’t experienced these “pit stops”, you haven’t been selling long enough. I’ve encountered them in most deals — the surprise witness whom we now need to accommodate or appease with a document, video, answer, asset or sworn affidavit. The worst part is most of these parties can’t says “yes”, but they all can say “no” so making them happy and jumping back on track is a challenge.
Gartner found that when asked if they ever revisit previously completed parts of the process during the buying process, more than 75% of buyers said yes to all four buckets. This is caused by information that surfaces and causes them to rethink what they thought they knew. These are the “what ifs” that throw a wrench in the advancement of buying.
And, how does our current toolset handle these pitstops? Offline and out of band. That’s somebody else’s problem. Edit the proposal for the 20th time after the email back and forth
The writing is on the wall. Our toolset is outdated. We’re chasing a snowball downhill and were coming to terms with the following
Big monolithic multi-page proposals are just shit. Absolute garbage. No matter how pretty they are, they attempt to be “one size fits all” and fail spectacularly at speaking to every dept they must
Most B2B organizations buy in a crazy non-linear way that can’t be articulated in a neat little 50-slide powerpoint
Proposing the ideal
Ultimately, we’re left without the right tools to do the job at hand. We need a way to sell into organizations that can adapt to this landscape. Not doing so is willful ignorance
Our requirements :
facilitate non-linear purchase processes
enable content creation from disparate sources
offer instant recall to decisions and assets irrespective of role
provide lenses into information for different departments and different roles
make it easy to assemble
make it repeatable
offer actions and encourage pitstops that add depth to the experience
We’re attempting to gather these features in software (Backdrop.io) and chipping away at the problem we and other sellers are presented (above)
Software Time (Selling with algebra)
We’ve been looking at tools that are inexpensive that can help us at Backdrop (https://backdrop.io) to sell more effectively and lately have been evaluating the idea of an ROI Calculator that our customers can use and we can embed.
We’ve found a couple studies that point to sales inefficiency - namely sellers spending too much time looking for documents. Since that’s quantifiable we’re going to explore next week at the equation we’re going to try to champion as a “sales device” and how we’re planning on sending to our customers.
Can you recommend a few that I should be looking at? What do you use?