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The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

By Jason Lemkin
Monday, May 26, 2025 | Blog Posts

The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

We’ve already seen something happen in support. You can’t automate 100% of support with AI yet. At least, not reliably. But you can automate 30%-40% of support for real … with top 10% CSAT.

So what does that mean for inside sales?

THE 2026 SALES TEAM

Can't Wait to See You Again Next May

SaaStr Annual 2025 was an incredible gathering of SaaS and AI leaders, and it was amazing to see everyone come together to share, scale, and learn. From groundbreaking AI demos to tactical sessions with some of the brightest minds in SaaS + AI, this year’s event truly raised the bar.

We’ll Be Back in May 2026:

For us, moving SaaStr Annual back to May has been about returning to our roots. The earlier timing allows us to focus on what matters most: creating the ultimate environment for learning, networking, and scaling. We had such positive feedback on-site surrounding May that we'll be back at the same time next year.

SEE YOU NEXT MAY

Dear SaaStr: Our Champion Left The Company. How Do I Ensure a Shaky Deal Doesn’t Collapse?

By Jason Lemkin
Sunday, May 25, 2025 | Q&A

When your champion leaves, you’re essentially starting from scratch with the account. You’ve lost your internal advocate, and now you need to rebuild trust and prove value to the new stakeholders. Here’s how you can stabilize the deal and prevent churn:

Treat it like a brand-new deal. This is critical. You need to resell the value of your product to the new decision-makers. Get on a plane if you have to, meet them in person, and make your case. Show them why your product is indispensable to their success. Don’t assume they’ll just continue with the status quo—they won’t.
Build multiple champions ASAP. One of the best ways to de-risk deals is to ensure you have multiple points of contact within the organization. If you’ve been relying on just one champion, this is a wake-up call. Start building relationships with other stakeholders—end users, managers, and executives. The more people who understand and value your product, the less likely the deal will fall apart when someone leaves.
Go There. In Person. This isn’t as magical as it is when your champion is still there. But go anyway. It says a lot when you show up in person.
Prove ROI immediately. The new stakeholders will want to know why they should keep paying for your solution. Be proactive in showing them the ROI your product delivers. Use hard data, case studies, and specific examples of how your product has driven results for their team. If you can tie your product directly to their KPIs, you’ll have a much stronger case.
Engage your executive team. If the account is large enough, get your executives involved. Get the CEO and VP personally involved now. This is especially important if the deal is at risk of churn due to a competitor aggressively courting them.
Over-communicate value. Don’t assume the new stakeholders understand the value of your product. Regularly communicate how your solution is helping their team succeed. This could be through quarterly business reviews, success stories, or even simple check-ins. The goal is to keep your product top-of-mind and indispensable.
Address any gaps head-on. If there are feature gaps or other issues that could jeopardize the deal, address them directly. Be honest about what you can and can’t deliver, and work with the customer to find a solution. Surprises are the fastest way to lose trust, so transparency is key.

Ultimately, the key is to act fast and treat this as an opportunity to strengthen the relationship. If you can successfully navigate this transition, you’ll not only save the deal but also set the foundation for long-term growth with the account.

KEEPING THE DEAL

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Perplexity’s CBO: Speed is The New Moat in AI Sales

By Jason Lemkin
Sunday, May 25, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Perplexity’s CBO: Speed is The New Moat in AI Sales

Perplexity’s CBO Dmitry Shevelenko joined Sam Blond ex-CEO of Brex at 2025 SaaStr + AI Summit for a deep dive on AI and Sales. More on the full session coming soon but this deep dive on being prepared for meeting prospects in the Age of AI was super interesting.

“Every question you would typically ask during a discovery call should now be asked of AI before the meeting.”The 90-Minute Meeting Prep is Dead

Here’s a hard truth every CRO, VP of Sales, AE and founder needs to hear: You have no excuse to not be moving faster.

While you’re spending 2+ hours researching prospects, reading through LinkedIn profiles, and manually preparing for sales calls, your competitors are using AI to compress that same preparation into minutes. The result? They’re having more conversations, closing deals faster, and scaling their businesses while you’re still stuck in research mode.

Perplexity’s CBO shared how AI is revolutionizing meeting preparation—and it’s not just about efficiency. It’s about unlocking what he calls “superpowers” that transform how founders approach every customer interaction.

THE NEW MOAT

3 Ways I’ve Changed Venture Investing at SaaStr Fund

By Jason Lemkin
Sunday, May 25, 2025 | Blog Posts

3 Ways I’ve Changed Venture Investing at SaaStr Fund

So I’m mostly made good investing decisions. My first VC investments were Pipedrive ($1.5B cash exit to Vista), Algolia (IPO candidate), Talkdesk ($10B last round, IPO candidate), Salesloft ($2.3B cash exit to Vista). And I have a few rocketships in the next batch, from Gorgias to RevenueCat to $1B+ Owner and more.

But also, over time, I’ve made more mistakes too. I had 2 relatively big losses that I just shouldn’t have. That were 100% avoidable. They don’t haunt you, but they hang over you.

So if interested — here are the changed I’ve made to investing at SaaStr Fund.

3 WAYS I'VE CHANGED SAASTR FUND

The Top 10 Strategies Toast’s CRO Uses to Crush Quotas

By Jason Lemkin
Saturday, May 24, 2025 | Blog Posts

So a little while ago Toast’s CRO Jonathan Vassil joined Sam Blond on SaaStr CRO Confidential on how Toast built one of the strongest but toughest rocketship in sales: a lower gross margin, lower ACV ($10k), sales-led SMB sales motion.

The company now serves approximately 85,000 customers and 140,000 locations using Toast across the US, Canada, and the UK, and has reached over a billion dollars in revenue while still having approximately 85% of the market left to conquer.

It doesn’t get much harder in B2B sales that an in-person, low-ish ACV sales … but Toast has … crushed it.

CRUSH QUOTA

Dear SaaStr: We’re At $3m ARR Growing 35%. What Does The Future Look Like?

By Jason Lemkin
Saturday, May 24, 2025 | Q&A

1. It’s going to be a grind.

At 35% growth, you’ll likely double ARR every 2-3 years. That means you could hit $6M ARR in 2 years and importantly,. $12M ARR in 4-5 years. While this isn’t hypergrowth, it’s steady. If you can maintain this pace and improve your metrics (like NRR and sales efficiency), you could still build a significant, valuable B2B business over time. However, you’ll need to be patient—it’s a slower path. And one VCs won’t be interested, and most buyers and Private Equity firms won’t be either until you cross $10m ARR or so.

2. Fundraising and Hiring Challenges

Raising a Series A or B at 35% growth will be essentially impossible. Most VCs won’t invest unless they see a clear path to 3x ARR in 12-18 months. Don’t even waste energy on thinking about raising VC capital unless growth later reaccelerates to “T3D2” levels or close.

And you won’t be able to attract mercenary hires that are just there to join a hot start-up. Adjust to that reality. Hire pirates & romantics that truly, deeply believe in your product and journey. And maybe that don’t come from all the usual places.

3. Operational Focus

At 35% growth, you need to optimize every dollar spent. Cut low-ROI initiatives and focus on your best-performing channels. Double down on upsells and cross-sells to improve NRR. If you’re selling to SMBs, churn can be a killer—fix it now. You’ll also need to hire carefully, don’t overstaff until you see faster growth.

4. Private Equity Sales & Other Exits

35% growth isn’t going to get many buyers interested at $3m ARR. But … but … at $10m ARR it starts to get interesting to Private Equity firms to buy you. And 35% growth at $20m ARR is very, very interesting to many Private Equity firms. So if you can keep it going, not fall behind the competition, and maintain that growth at $10m+ ARR, you may build into a very attractive exit. So long as you don’t raise too much capital.

Final Thoughts: Own It.

The future isn’t bleak, but it’s not easy either. If nothing else, you’re off the hook ”VC track” and the “hot start-up” track. Own that.

At 35% growth, you’re not on the IPO trajectory, but you can still build a profitable, sustainable business if you focus on efficiency and customer retention. And you can still make millions if you are careful not to raise too much capital and push the business to $10m-$20m ARR with efficient growth.

The key is to reignite growth where possible—whether through expanding your TAM, improving your go-to-market strategy, or doubling down on upsells. If you can’t accelerate growth, focus on profitability and long-term compounding. SaaS is a grind, but steady growth can still lead to meaningful outcomes over time.

MORE HERE

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