Sep 8, 2023 · 1h 1m · news
Doug Adamic: Why Discounting is BS; How to Reduce Sales Cycles and Create Urgency | E1058 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Brex Chief Revenue Officer Doug Adamic joins host Harry Stebbings to share tactical frameworks on scaling enterprise sales, designing rigid yet empowering playbooks, and driving pipeline velocity.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 17% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 3.5 Guest disagreement 1.8 Harry pushing back 2.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:54 Rejection of macro market premise
Doug explicitly states 'I struggle with that comment inherently' when Harry asserts demand creation is harder in 2023, arguing economic downturns are actually the optimal time to sell spend management.
Hardest push from Harry ▶ 46:43 Challenging rep surprise ruleHarry directly challenges Doug's assertion that being surprised by a deal loss is inexcusable, asking 'Do you think that's fair?' and offering a counterexample of unpredictable fundraising freezes.
Biggest teaching moment ▶ 27:23 Deconstructing discounting trapsDoug dismantles the common sales reliance on discounting to force urgency, explaining to host and listeners how discounting demeans value and ruins conversion economics.
Harry holds his own ▶ 48:48 Board-level perspective on deal slippageHarry uses his position sitting on startup boards to call out the recurring revenue leader excuse of deals slipping into the next quarter.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Falling in Love with Sales | 2 | 2 | 1 | 1 | Harry asks open-ended questions about Doug's career trajectory across Cintas, SAP, and Concur. Doug gently reframes whether sales is loved instantly or learned over time as complexity is understood. | |
| The Art of Listening and Discovery in Sales | 3 | 3 | 1 | 1 | Harry cites specific feedback from prep calls regarding Doug's minimal word count on discovery calls. Doug breaks down how his enablement department dissects sales calls into bite-sized steps. | |
| Creating High-Quality Pipeline and Demand | 3 | 4 | 2 | 2 | Harry asks about pipeline goal setting and references his own experiences with poor quality leads. Doug counters standard sales advice requiring 5x-7x coverage, showing how high quality and high conversion allow orgs to operate under 1x coverage. | |
| Creating Demand and Navigating Harder Markets | 4 | 4 | 4 | 4 | Doug directly challenges Harry's premise that demand creation is harder in tough economic times, arguing downturns are ideal for spend management. Harry pushes back, noting buyers are closed-minded and budget-frozen in current markets. | |
| Threading the Needle and Identifying Real Buyers | 3 | 4 | 2 | 2 | Harry asks how to identify real buyers without being transactional or aggressive. Doug details pragmatically testing buyer reality by asking when they last implemented a similar tool and utilizing constructive tension. | |
| The "Trips to the Bank" Philosophy and Playbook Adherence | 2 | 3 | 1 | 1 | Harry asks Doug to explain his aphorism about taking trips to the bank. Doug articulates his philosophy on rep efficiency, capacity, and playbook adherence. | |
| Creating Urgency and The Truth About Discounting | 4 | 5 | 3 | 2 | Harry poses a direct question on whether sales leaders should use discounting to force urgency. Doug firmly rejects discounting as a short-term hack that demeans value and sets dangerous precedents. | |
| Going Faster and Overcoming Sales Bottlenecks | 3 | 3 | 1 | 2 | Harry asks Doug to unpack speed bottlenecks and evaluate rep talent versus tooling. Doug defines the primary bottleneck as reps selling feature functionality rather than changing customer buying criteria. | |
| Defining and Transitioning the Sales Playbook | 3 | 3 | 1 | 1 | Harry asks Doug to define a sales playbook and when to transition playbooks as companies scale. Doug explains tracking operational residue data and restricting updates to quarterly boundaries to avoid disruption. | |
| Inspiring Teams Beyond the "Wolf of Wall Street" | 3 | 4 | 2 | 2 | Harry asks about quarterly motivation using Wolf of Wall Street tropes. Doug reframes rep motivation around deep personal goal setting rather than performative chest-beating. | |
| Customer Success Hand-offs, Expansion, and Deal Reviews | 4 | 4 | 1 | 2 | Harry brings up ZoomInfo CEO Henry Schuck's observations on CS shifting from easy upsells to rigorous ROI proof. Doug concurs and outlines Brex's structured hand-off process and value engineering. | |
| Winning, Losing, and Predictability in Sales | 5 | 4 | 3 | 5 | Harry explicitly challenges Doug's view that losing a deal due to surprise is inexcusable, presenting a scenario where a CEO suddenly freezes budget due to funding troubles. Harry also draws on his experience sitting on tech boards to challenge quarterly deal slippage. | |
| Leadership Evolution and The Human Aspect of Sales | 3 | 3 | 1 | 2 | Harry probes the human unpredictability of revenue leadership and hiring tradeoffs between domain and segment expertise. Doug shares his 'box score' management mindset. | |
| Founder Pitfalls, AI in Sales, and Quick-Fire Round | 3 | 3 | 2 | 1 | In a quick-fire round, Harry asks about founder hiring mistakes, AI, and changing sales tactics. Doug explains why founders fail when expecting reps to sell without supporting enablement structures. |
Statements from this episode (28)
Adamic: Loving sales is learned over time through understanding customer outcomes
“I think you need to be, have an entrepreneurial spirit in general to go into sales. But I think once you understand what sales is all about, improving a customer's business by driving specific outcomes, You recognize how complex it is, how intricate it is, and…”
Adamic Scaled Concur From $50M to $1B Revenue Before SAP Acquisition
“I joined when we were about 500 people, and about 50 or sixty million dollars in sales and we grew back to almost a billion dollars before we were bought by SAP.”
Adamic: Disruptive Sales Requires Shifting Customer Buying Criteria to Your Product
“How to be able to describe something that's different where maybe customers did not understand the business challenge or business pain that they had was probably the biggest takeaway, like changing the buying criteria to lead to your product.”
Adamic: Evaluate sales calls in bite-sized steps rather than totality
“When we're looking at a sales call, it's very difficult to look at it in Totality. We break it up into bite-sized steps and then be able to critique whether or not we are doing the things to get access to unique information that we can be able to determine whe…”
Adamic: Demand creation is the responsibility of all go-to-market teams
“Everyone's responsibility is demand creation. So I have three major objectives that I tie My entire go-to-market distribution team too. One is advanced demand creation. Two is the profitable conversion of that pipeline. And then three is the protection and gro…”
Adamic: SAP Concur Operated With Under 1x Pipeline Coverage
“Everyone talks about like, you need that five X pipeline, you need that seven X pipeline in order to make your goals. Not necessarily. When I left Concur and where I'm trying to drive Brexit, we had less than one X pipeline going into a quarter because we knew…”
Adamic: Economic downturns are the best time to sell spend management software
“I think that those are the best times to create demand. When you are focused on being able to drive value in regards to investments a company makes in giving employees money to spend on their behalf, the tighter the times are, the more they need to pay attenti…”
Adamic: B2B Buyer Conversion Now Requires 16 to 20 Touchpoints
“Maybe five, seven years ago, you used to touch an individual four times or five times, but, or they would convert into wanting to learn more about your business. Now we're up to like, 16 or 20 times to be able to do that.”
Adamic: Prospects Unable to Detail Past Implementations Are Not Economic Buyers
“Asking that individual the last time they, for instance, implemented something similar to Brex, and then just listen. And if they don't have a precise or concise answer, or can't point back to something that they did, then you probably are not talking to the b…”
Adamic: High-performing sales campaigns require constructive tension with prospects
“You have to be okay with constructive tension in a sales campaign, and if you don't have constructive tension in a sales campaign, then you're probably not introducing something that's pushing the boundaries of the thinking of the group you're talking to.”
Adamic: Sales playbooks allow reps to sustain earnings as quotas increase
“If I do my job correctly and you lean in on the playbook, And you follow the rules that have been set up. Technically, you should be able to get more done in a day to be able to make more frequent trips to the bank to make bigger deposits because that's why yo…”
Adamic: Companies Buy Software For Only Three Specific Reasons
“There's only three reasons why An organization will make a purchase. They're in trouble right now, they see trouble coming, or an individual or group wants to be made a hero and get ahead of something.”
Doug Adamic: Brex does not rely on discounting to close deals
“Brax, for instance, has been able to deliver on that over and over again, So I don't feel as though I need to overly discount in order to be able to add value to an organization or create that compelling event.”
Adamic: Sales reps must increase sales velocity when quotas rise and territories shrink
“When quotas go up and territories shrink, Have, that's the definition of growth. Then the only way for you to be able to make more money is to go faster.”
Adamic: Biggest sales training challenge is stopping reps from pitching features
“If you don't understand how to change the buying criteria to lead to your product rather than leading with your product, then I think that's the biggest challenge, at least that I have in building and training a sales force is to refrain from being excited to …”
Adamic: Skipping sales playbook steps inevitably harms customer partnerships
“If you skip a step or you skip checklist items, it's going to reveal itself at the end. And it's not that you're trying to convince a company or trying to You know, trick a company. This is honestly the fact that if you miss a step down the way, then that part…”
Brex created a department specifically to catalog sales playbook feedback
“One of the departments that we built actually catalogs those things, and then when they build up to a specific level of residue, we figure out when is the right time to be able to augment the playbook and then be able to re-enable the teams and introduce that …”
Adamic: Sales Playbook Changes Should Never Be Introduced Mid-Quarter
“I don't introduce anything in the middle of a quarter. I'll only introduce something at the beginning of a quarter. There are certain things that are too disruptive to introduce in a quarterly basis, so we'll take those half year or full year.”
Adamic: Executive deal sponsorship should be shared across leadership, not just CEOs
“There are always going to be marquee organizations that are going to require a level of attention or connectivity to a company at that level, but if I'm holding myself accountable as a CRO, we will want to have executive sponsorship with all of our marquee org…”
Adamic: Customer trust is destroyed if sales prioritizes vendor benefit over outcomes
“The second a customer thinks that you are trying to do something that's benefiting you personally or breaks versus actually serving the customer, then all trust is lost.”
Adamic: Account expansion is a byproduct of executing core customer promises
“Add-ons expansions, purchase of other products or categories of products are a byproduct of doing all of this other stuff really, really well.”
Adamic: Good Salespeople Are Never Surprised By Losing a Deal
“If you are running a proper deal, you shouldn't be surprised, and if at the end of a campaign, insert whatever it was that surprised you, that is a bad reason to lose a deal, because if you're good at your profession, You should never be surprised as to why yo…”
Adamic: Salespeople must know target customers' financial situations
“To not know what the financial aspect or pattern is of the organization you're selling to is inexcusable.”
Adamic: Focus on daily execution inputs rather than quota metrics to drive sales
“So in, in my family, we have a saying, it's not the score. It's not the box score that the thing that you focus on. It's all the little things that the box score doesn't have, because if you do those little things, the box score takes care of itself. Every sin…”
Adamic: Balance Industry Experts With Domain Newcomers to Build Top Sales Teams
“When you can balance some experience with the right type of person, with someone who has segment experience, but no, not industry experience, that's when you get your best, most innovative and sort of interesting sales campaigns and structure and distribution …”
Doug Adamic: Sales reps perform poorly without supporting teams and enablement
“A salesperson on and to themselves aren't going to sell well on average. They need to be supported by a team of people that tools them correctly, and then that works much better.”
Doug Adamic: Salesforce remains the gold standard for enterprise sales strategy
“I still am impressed by salesforce.com and how they go about getting business, how they sell value, the way in which they create an experience and a customer success motion for the companies that they have, the breadth and depth of how they can add value and s…”