Jan 3, 2018 · 32m · saastr
Secrets to Closing Your First 6 Figure Deal
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Hosted by Salesforce Ventures, this executive panel provides SaaS founders with strategic guidance and tactical methodologies for closing their first six-figure enterprise deals. Industry leaders share actionable insights on navigating legal and procurement hurdles, aligning internal operations, and qualifying high-value enterprise accounts.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 1.1 Guest teaching 2.0 Guest disagreement 0.1 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:13 Lord contrasting mid-market contract flexibility against enterprise demands
Kathy Lord presents a mild counter-perspective to Jon Stewart's concession on customer paper by explaining how Intact forces upper-mid-market clients onto standard vendor terms.
Hardest push from Jason ▶ 29:14 Host playfully responding to Salesforce ecosystem shoutoutBrooke Gardner lightheartedly quips that she did not pay Stewart for highlighting Salesforce's infrastructure as his core credibility asset.
Biggest teaching moment ▶ 3:43 Stewart breaking down hidden legal and procurement barriersJon Stewart explains to the audience that enterprise sales readiness is fundamentally constrained by procurement hurdles, click-through license mismatches, and 65-page master agreements rather than product capability.
Jason holds their own ▶ 32:11 Host connecting panel advice to Salesforce ecosystem boothBrooke Gardner neatly ties the operational and architectural security advice of the panel directly back to the Salesforce ISV partner program.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Panel Introductions and Executive Growth Backgrounds | 1 | 1 | 0 | 0 | Brooke Gardner introduces the panel and asks standard introductory background questions. The panelists share their companies' growth trajectories and enterprise sales experiences collaboratively. | |
| Recognizing Readiness to Pursue Six-Figure Enterprise Deals | 1 | 2 | 0 | 0 | Jon Stewart humorously reframes the prompt by pointing out that startups are never truly ready for their first enterprise deal due to legal and procurement realities. The conversation remains supportive and instructional. | |
| Key Milestones and Prerequisites for Enterprise Readiness | 1 | 2 | 0 | 0 | Bob Marsh notes that readiness is largely a mental decision rather than a single technical milestone, while Kathy Lord and Jon Stewart share concrete operational shifts. The panel maintains high rapport with the moderator. | |
| Actionable Advice for Securing First Six-Figure Deals | 1 | 2 | 0 | 0 | The guests deliver pragmatic tips on pricing, meeting preparation, and managing enterprise procurement hurdles without any pushback or confrontation. | |
| Audience Q&A: Enterprise Transparency and Customer Selection | 1 | 2 | 0 | 0 | Brooke facilitates an audience question about transparency with early enterprise prospects. Bob, Jon, and Kathy detail why honesty builds leverage and alignment, maintaining a collaborative tone. | |
| Audience Q&A: Navigating Legal Agreements and Contract Redlines | 1 | 3 | 1 | 0 | Jon Stewart details critical legal deal terms like IP assignment and indemnification, while Kathy Lord offers an alternate upper-mid-market tactic of standing firm on standard paper. | |
| Audience Q&A: Targeting High-Probability Enterprise Accounts | 2 | 2 | 0 | 0 | The panel answers an audience question about overcoming startup longevity fears with source code escrow rather than sharing financials, followed by Brooke closing the panel with Salesforce booth announcements. |
Statements from this episode (17)
Marsh: Sales success requires daily discipline, which only 15% of reps have
“What made them do well is not from any magic closing technique or some special product or relationship. It's that they had the discipline to do the controllable activities every single day with discipline that led to success. So, as I learned, but the problem …”
LevelEleven grew from one six-figure customer to a dozen in one year
“So in the last year we've gone from One six figure customer to now we have about a dozen. We just recently signed our first quarter million dollar customer.”
Stewart: Enterprise deals are won on procurement process, not just product
“The lesson learned there is understand early on, you know, the answer to the question, which is, how do you guys buy software? Because when you attack those, it's never about the, ah, necessarily winning the technical end of it. It's gonna be about everything …”
Marsh: Founders must personally run their startup's first enterprise sales cycles
“Particularly for that first one, or those first handful, and probably it'll last for a long time, you will need to own that sales process, and honestly, the larger enterprises will expect it and they'll value it too, but you're gonna probably need to take owne…”
Marsh: Readiness for six-figure deals is primarily an emotional decision
“I really think it's the, a little bit what John said, like, it's, some of it is the emotional decision that you're ready. And that you're willing to go for it.”
Stewart: Founders must embrace 'CEO magic' for their first enterprise deal
“For your first enterprise account, expect to be doing CEO magic, and do a lot of it, and don't shy away from it.”
Stewart: SMB software solutions are rarely technically ready for enterprise clients
“What you're gonna find is, if you have an SMB, a mid-market solution, and you bring it to that enterprise segment, your solution's probably not ready either.”
Marsh: Enterprise deals take six months of procurement after a verbal yes
“Go to that meeting, expect there to be many more people that you need to deal with, and ultimately when they say yes, it actually doesn't mean they're ready to go. It might mean like, yes, we want to buy it, and it'll take six more months to go through procure…”
Stewart: Sponsor pricing is meaningless until corporate procurement takes its discount
“And the price, whatever you negotiate with your business sponsor, doesn't mean a darn thing until you get through the corporate procurement Department, and they get their pound of flesh, which they will.”
Stewart: A startup's first enterprise client must be referenceable to win others
“You are gonna use that first enterprise client, ah, to get your second, third, fourth, and fifth, and so they've gotta be a referenceable customer.”
Marsh: Tell prospective enterprise buyers they are your first customer
“No, I actually do think that you should. I think it's, you want them to know that. I mean, if they don't, it's, they're gonna buy, I mean, if you tell them that, then a lot of these bigger companies, they actually like that, and they're comfortable with that, …”
Lord: Closing the wrong first enterprise deal can derail product development
“Is that prospect The right first six figure deal for you to close because you need somebody who's a little bit of a visionary who has a high risk tolerance that's willing to truly partner with you to help you bring your organization to service those types of c…”
Stewart: SaaS startups must strictly avoid IP assignment rights in enterprise contracts
“Absolutely no IP assignment rights, and these are ones that are important, guys, right? And because large enterprise companies will be really sneaky about that and try to stick that in there, i.e., you build a feature for them, they own it, or it can make an a…”
Stewart: Enterprise no-hire clauses are not enforceable in most US states
“The no hire clauses are kind of BS. They're not really enforceable in most states.”
Lord: Startups must use the buyer's contract paper for mega-cap customers
“I agree when it's the Boeing's, the GE's, I mean, you gotta use their paper.”
Lord: A prospect's tech stack reveals their risk tolerance before sales calls
“So what are the other technologies do they use? Are they cutting edge? Are they using sort of the latest and greatest and Implementary technologies, and that just says a lot from the outset, even without having had conversations with them to know, you know, wh…”