Opinion
Fillmann: Founders Should Hire Sales Reps Individually, Not in Competing Pairs
“If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you're trusting them, that you've got their back. And if you have two different people kind of competing in the same environment, I don'…”
Insight
Fillmann: Teaming Two Sales Alphas Together Will Crash and Burn
“I think for me I'd say the biggest mistake I've made was trying to team people together that were both alphas. And like, I think being an alpha in sales is really, really good. You want the natural leader, but if they do it at the expense of other people and t…”
Insight
Fillmann: Prioritize Potential Over Experience, Except for Mature Enterprise Accounts
“It's always hypo one experience to the, there's always an exception to that though. I think when you have like a big mature customer and a big brand with a lot of visibility, You'll always have to take experience first. You don't want someone learning on the j…”
Insight
Fillmann: Retraining Non-Enterprise Reps for Upmarket Selling Fails
“Trying to train folks that don't have the enterprise experience and convert them over, I don't think it's setting them up for success. I think you need to be able to find folks that have done this before that bring in the top end of the game and then having re…”
Insight
Fillmann: Industry Expertise Matters More Than Prior Deal Size Experience
“Industry experience and driving client trust and relevancy, you can reverse engineer everything a lot easier than having big experience on a deal, but not understanding what's going to make your customer successful.”
Insight
Fillmann: Competitive Sales Roles Build Bulletproof Skin for Beginners
“And then my first role at IBM was a competitive sales rep. So every account I talked to didn't want to talk to me. So you get to kind of have this like bulletproof skin on you, which is a really, really great way to get into sales.”
Insight
Fillmann: Enterprise Clients Care About Their Metrics, Not Your Product
“Clients don't care about you, your gear, your product, your organization. They care about them, their metrics, their firm. And so it's gotta be client oriented.”
Insight
Fillmann: Solving Unknown Customer Problems Eliminates Direct Sales Competition
“It's about identifying problems a customer has that they don't know how to solve, creating a vision, and then encouraging them that you have an opportunity to solve that problem for them. And now you're hunting for a way larger pot of money and you're actually…”
Insight
Fillmann: Enterprise Buyers Want Role-Specific Value, Not Software Demos
“If you want to drive client relevance and you're going to show up to an insurance firm, and you're going to work with like an insurance claims adjuster, they don't want to see a demo of technology. They want to know, how do you make the life of a claims adjust…”
Insight
Fillmann: Industry-Focused Playbooks Compress Enterprise Sales Cycles
“If you identify the TAM and you create a vision and you put an industry lens on it, the client gets engaged faster and the rep Gets to go a lot faster. It actually compresses the sales cycle, and now you're finding where the dollars are in April, May, or June,…”
Insight
Fillmann: Ask Interviewed Sales Reps for Referrals to Find Top Talent
“Whenever you're on the interview cycle, the first question I always ask full stop is, hey, top rep, who are your friends? And should I have an opportunity to meet them? Because they're always going to know the best talent.”
Insight
Fillmann: Target Latent Demand to Expand TAM Without Increasing Headcount
“You go look at the demand that's inbound, and then you look at the latent demand that doesn't exist. That's an immediate way to increase the TAM that you're pursuing without hiring any more people.”
Insight
Fillmann: Sending Price Proposals Early Derails Negotiations Into Price Haggling
“So I think the biggest mistake is when you just send a price over, right? And then you end up arguing about numbers that you ever see this, you send a proposal, And whether it's like a percentage savings or the absolute number, it's like human nature in negoti…”
Insight
Fillmann: Enterprise Sales Information Asymmetry Became Obsolete 20 Years Ago
“Protectionism. I think, like, things are a lot more transparent. Customers have access to all kinds of data about your organization, about products, about negotiation. So, like, the idea of being closed-ended, like, you have all the information and you don't w…”
Insight
Fillmann: Waiting a Full Quarter to Give Feedback Never Lands Well
“It's also less about waiting a whole quarter and giving feedback, which I think it's really hard, and it never lands well.”
Insight
Fillmann: Junior Reps Gain Three Years of Experience Paired With Alphas
“I want to be able to pair that person with someone who might say, you know what? I don't have as much at bats. Like I don't have the experience pair me with them. And they're going to exponentially learn. They're going to get three years of education in a year…”
Disclosure
Fillmann Clears Two to Three Unscheduled Hours Daily to Assist Reps
“A big part of my day is I clear two to three hours that I have no plans for, specifically so a rep says, hey, I've got a big account meeting coming up, and I feel stuck, or I have an account meeting coming up, and I want you to join, I can immediately, I will …”
Insight
Fillmann: Expecting New Reps to Close 18-Month Deals in Year One Fails
“If it's a one to two year sales cycle and you have someone new, maybe it's more of an 18 to 24 month sales cycle, So if you put them in with the hope that they're going to land it in the first year, you're setting them up for failure.”
Insight
Fillmann: A Sales Rep's Q1 Performance Determines Their Full-Year Success
“What you do in Q one completely determines the success of your year.”
Insight
Fillmann: Create Deal Urgency by Working Backward From Client Go-Live Dates
“And if you actually take that very logical objection of, not now, we're six months away, and you programmatically work back, and you create a success plan based on their timeline, chances are they need to get going right now. But like, you can't make the assum…”
Insight
Fillmann: Enterprise Sales Proposals Must Be Tailored to the CFO
“Because that's like the new, we have a new buyer in the cycle that was never there. That's the CFO. And they're probably going to get personally involved in an enterprise deal that's material. And if you haven't evaluated that and haven't like role played that…”
Insight
Fillmann: Accurate Sales Forecasting Requires Math Models, AI, and Qualitative Analysis
“I think there's three pieces. One is you need like a very left brain math model that looks at all the historicals and says, you know, like on an average ratio, this is our close rate to pipe. Like there's basic math that everyone should include as part of the …”
Insight
Fillmann: Align Deal Reviews With Reps' Personal Financial Goals Over Quotas
“The first question I ask on a big deal review is, what's your goal? Not your quota. What's your goal? What do you need to be financially successful this year? Great. Now, how do we get there? Here's this proposal. You're not going to get there with this propos…”
Insight
Fillmann: Executive Top-to-Top Alignment Must Happen Before Deal Time
“The other thing you want to do is have really good top-to-top alignment. And I don't mean when it's deal time. I mean, like, before it's deal time, where there's a thoughtful conversation of aligning, whether it's the CEOs together, or the CIOs together, or li…”
