Insight
Cranny: Enterprises have built-in rejection mechanisms against viral software
“It's typically because there's, you know, they, they're set up to reject. It's like there's a rejection organism based on politics, other decisions, standards, security, things of that nature, as far as how it affects everyone.”
Insight
Cranny: Delaying deals is better than losing accounts to entrenched incumbents
“In fact, the sales campaigns I've been involved with, some of my best efforts have been around stopping deals from getting done versus actually getting them. Because once these big investments are made, I mean, it can be a long time and in a lot of cases, neve…”
Insight
Cranney: Early startups must hire reps who create playbooks from scratch
“Somebody that gets excited about doing this exact thing, it's typically not the one that's been running in somebody's playbook. It's the one that really understands how to go create that playbook from scratch.”
Insight
Cranny: Relying on bottom-up adoption without sales is short-sighted
“The need may not be there, but I think CEOs might be being pretty short-sighted that there's not going to be competition down the line, particularly as they try to expand inside a account.”
Insight
Cranny: Top sales hires often come from military or sports backgrounds
“So competitive, high courage, focused discipline, people that have a little bit of charisma, you know, a lot of intellectual horsepower and can think quickly on their feet and people that can take a beating, right? That they can actually go in and take a lot o…”
Insight
Cranny: Enterprise sales champions must actively advocate behind closed doors
“A champion is really someone that if I leave that account or close the room and they're going to have a vote to move to the next level and or to buy from my company over something else, that that champion is actually somebody that has the influence and the cap…”
Insight
Mark Cranny: Enterprise tech sales mirror political campaigns' complex stakeholder dynamics
“It's a lot like enterprise sells for campaigns selling to, you know, large enterprises. You got to get a lot of different people on board in these complex selling situations and essentially get them to vote for you on the tech sell side.”
Insight
Mark Cranny: Bottom-up startups risk displacement without up-market expansion
“You can have that, you know, that beachhead established, but if you're just spending all your time going to establish another beachhead at another company, you're at risk of getting pushed out by the incumbent and or somebody that's got that organizational con…”
Insight
Mark Cranny: Startups fail sales cycles by ignoring competitor depositioning
“And if you don't really know how they're depositioning you can go through a whole cycle and come up empty at the end because they've laid the traps. They've set the criteria. And if you don't know enough about your competition to understand when you're walking…”
Insight
Craney: Startups wait too long to define free versus paid feature boundaries
“I think in a lot of cases, we see companies wait too long to start thinking about and drawing that line so they can get to a premium type offering.”
Insight
Cranney: Startups always pay for go-to-market execution one way or another
“You're paying for it either way, right? You're paying for it by giving everything away for free. Cause you're not investing in sales and marketing, or you're going to have a channel partner do it, which you're giving your margin away. Somebody's paying for it.”
Insight
Cranney: Lowering high prices is easier than raising low prices
“It's way easier to go down than it is to go up.”
Insight
Cranney: Enterprise quotes must model full deployment pricing early
“In almost any proposal type situation, we wanted to Have not only your initial pricing per unit set, but you need to go model and understand what would happen if that customer adopted throughout their entire enterprise. Now early on, it sounds like a pipe drea…”
Insight
Cranney: Generic sales hires cannot figure out early product pricing
“And, you know, so I'd be a little careful to say any sales and or marketer is going to be able to figure this thing out for me. Cause it, you know, it does take somebody that's a little more intuitive that, that isn't taking shortcuts, you know, somebody that …”
Insight
Cranney: Hiring sales reps from similar mature products is a trap
“One trap a lot of CEOs or founders might fall into here is I'm going to go hire somebody that's selling something similar to what I sell.”
Insight
Cranney: Startups must review win-loss reports at least quarterly
“If you're not reviewing, you know, a win loss type report on a monthly, at least a quarterly, you know, some kind of fairly frequent cadence, depending on what's going on in your business and in the market and doing the postmortems on both sides of that. I thi…”
Insight
Cranney: Deal sizes must be large enough to fund direct enterprise sales
“If it's something that requires you to come in high and move left and right and be agile in the organization as well as up and down, and because of the complexity is, that typically means there's also going to be a big outlay, either cap, capital and or Operat…”
Insight
Cranney: Bottoms-up startups often fail going upmarket due to sales leadership
“It's very common on the inside type bottoms up motion that particularly as you, they build out the management that sometimes you, they'll miss moving up market because the BP might not have that skillset, you know, to go build out that next level.”
Insight
Cranny: Sales reps must walk client halls to map enterprise needs
“And you don't get that sitting in a cube in, you know, San Francisco or Silicon Valley. You get that from walking the halls Of these big organizations and really understanding, you know, what their initiatives are and how you're to be able to map up what your …”
Insight
Cranny: Restricting sales rep territory sizes increases productivity and win rates
“And actually, they get more productive the less territory they have, the less amount of accounts that they have, because they're able to, it kind of forces the situation to do, you know, where you're penetrating deeper into accounts, getting a lot more intimat…”
Insight
Cranny: Do not hire a scaling VP of sales before product-market fit
“The problem with getting a real VP of sales or a big executive too early is they're there to scale, and if you're still wandering around a little bit in the desert trying to figure out the fit, you might be a little early there.”
Insight
Cranny: Innovative startup products rarely have pre-existing enterprise customer budgets
“Particularly in a startup and or high growth situation where I'm selling something that's completely new because of a platform shift, it's a new way of doing things, is there's not recognition of that new way of doing things. And very common in my career where…”
Insight
Cranny: Late enterprise sales entries require immediate executive escalation
“If the party's already begun and I'm behind and competitions come in and define the criteria, I do not have The time and cannot afford to be working bottoms up in an organization. I've got to escalate and get high to see if I can get in.”
Insight
Mark Cranny: Uninfluenced enterprise RFPs are usually a waste of time
“If I'm getting an RFI, if I'm getting an RFP, and I haven't gotten out in front of it and influenced that, I've probably wasted my time.”
