33 GTM Lessons from Salesforce, Samsara, Legora and More

Over the last few months, founders and operators from Salesforce, LinkedIn, Notion, Webflow, Samsara, Legora and more sat down with us on the GTMnow Podcast. Between them, they’ve sold three companies to public acquirers, found over $100M in pipeline from leads nobody was working on, and trained a marketing team that has built 113 AI agents.

We went back through every conversation and pulled out the 33 lessons worth keeping. Each one is in the guest’s own words.

We grouped them into eight themes: sales and pipeline, AI, hiring, marketing, pricing and traction, leadership and career, fundraising, and customer success. Read it straight through, or jump to the one you’re working on right now.

Your top 20% know how to win deals, while the other 80% are guessing.

Your strongest performers carry your KPIs by running the same playbook on every deal, while you’re spending years (and money) trying to clone them. Meanwhile, across the rest of the team, deals stall, single-threaded with thin business cases and mutual action plans that don’t get actioned.

Accord makes your top performers’ playbook the whole team’s standard. Shaped by your unique sales process and real-time buyer conversations, Accord Agents handle the work between calls to move deals forward, so reps can focus on their buyers, and the conversations that close deals.

Accord brings agentic execution and the buyer experience together in one platform, turning how your best reps sell into how your entire team executes. Accord customers see an average 40% increase in deal size and 20% faster sales cycles.

Ready to be next? Visit inaccord.com

Sales & pipeline

1. Point agents at the leads nobody works.

“We score 1 to 5… ones and twos are our lowest… So we said, let’s have our engagement agent reach out to those customers. And in about eight months time, we drove over 100 million in pipe that was totally unseen otherwise… And it just found money.”
– Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products at Salesforce

2. Send less outreach to better-chosen buyers.

“We could be doing less outreach than ever before. We could be way more selective in who sellers… reach out to, because we’ve got that much more signal on what is going on for them.”
– Catherine Flynn, VP Marketing, Sales Solutions at LinkedIn

3. Reach out within hours of a job change.

“…top sellers are reaching out within hours, not days or weeks of a job change.”
– Catherine Flynn, VP Marketing, Sales Solutions at LinkedIn

4. Disqualify honestly. A lot of those deals come back.

“A lot of our largest customers today were people that we disqualified at the time… And then they came back to us maybe six months, 12 months later, or even a different role.”
– Ross Rich, Co-founder and CEO at Accord

5. Use pay mix to show reps what they control.

“Oftentimes people think pay mix is just an easy split that adds up to 100, but it’s actually a signal to the sellers of what they have influence over.”
– Brian Le, Global Sales Compensation Partner at Notion (now GTM Strategy & Planning Lead at Lovable)

6. When reps go off track, check the comp plan first.

“If you see reps not doing the things that you want them to do, then it’s not going and checking with the rep. It’s really going and checking your comp plan because that’s what the comp plan is telling them to do.”
– Siva Rajamani, Co-founder and CEO at Everstage

AI & agents

7. If you still prompt it, it isn’t an agent.

“We’re still prompting and asking questions. That’s not an agent, right? To me, an agent is when you have offloaded all your worries for that workflow, for that role at a company, and you can do it continually at a high rate of success.”
– Elias Torres, Co-founder and CEO at Agency (now CPO at Klaviyo)

8. Fix your data before you bolt on AI.

“The overall data is not there. It’s not filled to 100%. The data that’s there is not fully accurate… So if you really were to just bolt on AI to any of your internal systems, CRM is an example. It is going to give you accelerated nonsense.”
– Siva Rajamani, Co-founder and CEO at Everstage

9. Train every team to build agents. Don’t centralize it.

“You could create a team that just does it. You could have a team of experts and you just train them. And then marketing generates ideas and they go build it. But I don’t think you scale that way… if you train all of them to do their own and build their own agents, you get to a place where we are, where we’ve transformed much more of the organization.”
– Meagen Eisenberg, CMO at Samsara

10. Give the whole company a day to build.

“…we have a full-day builder day where we’re actually telling the full company, sit down, identify the top workflow you want to fix, and spend a whole day building it.”
– Linda Tong, CEO at Webflow

Hiring & building teams

11. Ask candidates what they’ve built.

“I always ask what people’s favorite tools are, what they’ve built themselves, how they build, how they think about prototyping. It’s a lot of the ‘how’ questions.”
– Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products at Salesforce

12. Tie top performance ratings to building with AI.

“You can’t get a 4 or 5, the highest rankings, unless you’re actively working with AI building agents.”
– Meagen Eisenberg, CMO at Samsara

13. Anti-sell the job to see who really wants it.

“Be like, this place sucks… you have to work a lot… Are you sure you want to be here? And so I think really that anti-sell sometimes will end up sharing a lot of information about whether they are really into this.”
– Shensi Ding, Co-founder at Merge

14. Sell it yourself before you hire your first rep.

“So if you outsource your initial sales to a sales person, you don’t really understand… you’re not really understanding the feedback that you’re getting from the field and why it’s not hitting in the beginning because it won’t hit… it just won’t resonate immediately unless you are very, very lucky.”
– Shensi Ding, Co-founder at Merge

15. Be most careful with the splashy senior hire.

“When I think about things that have set us back the most or hurt the business the most… it’s when you make a big, splashy hire and you wake up 6 or 8 months later and you zoom out and you go, oh my God… We’ve gone absolutely nowhere. And this person has hired a ton of people who maybe are also not the right fit for the same reason.”
– Ryan Denehy, Founder and CEO at Electric

Marketing & brand

16. Go where your competitors aren’t.

“Go where your competitors aren’t… these channels or these tactics are cyclical, right. Everybody rushes in to do field marketing. That’s going to decrease in effectiveness. So what’s the thing they’re not doing right now.”
– Keith Putnam-Delaney, Co-founder and CEO at Primer

17. Borrow credibility from people with an audience.

“One of the fastest ways you can grow is buying that credibility from people who already have the audience, as opposed to trying to create it yourself.”
– Keith Putnam-Delaney, Co-founder and CEO at Primer

18. Feed your ad platforms CRM conversion data.

“It’s going to optimize for whatever signal you feed it… So you have to feed it basically CRM conversion data back into the ad platform.”
– Keith Putnam-Delaney, Co-founder and CEO at Primer

19. If you win pilots but nobody knows you, spend on brand.

“The biggest issue that we had was people didn’t know who we were… And so for us, it’s just can we get into a pilot. And when we get into a pilot our conversion rates are incredibly high… There were too many deals where we just weren’t playing because people didn’t know who we are.”
– Patrick Forquer, CRO at Legora

Pricing & traction

20. Let your price point pick your sales motion.

“This is a high-priced product but also a very complex product, which meant we had to sell it with a direct sales motion… An AI-native product suite meant that the actual unit price on what we were selling was way, way lower, which meant that the economics, even though the margins were higher, the economics didn’t support a direct sales motion.”
– Ryan Denehy, Founder and CEO at Electric

21. Move to outcome pricing at your customers’ pace.

“I think in the future it’s going to flip and I think it will be more and more outcome-based and that will be consumptive in nature… But I don’t want to get too far ahead of where our customers are or want us.”
– Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products at Salesforce

22. Pay accelerators on the deal terms you want most.

“One of the things that we’ve optimized for is the multi-year contracts… So they get accelerators on those multi-year contracts… more than 85% of our customers are on multi-year contracts with us.”
– Siva Rajamani, Co-founder and CEO at Everstage

23. Find the channel, not just the customer.

“Product market fit has as much to do with finding the right distribution channel as it does with finding the right end customer.”
– Ryan Denehy, Founder and CEO at Electric

Leadership & career

24. Spend time in a GTM function that isn’t yours.

“Get out of your lane and get experience in some of the other GTM functions… I wouldn’t have the job I have today had I not sort of gone outside of my comfort zone and run a sales team or led a CSM team.”
– Catherine Flynn, VP Marketing, Sales Solutions at LinkedIn

25. Choose who you work for over what you work on.

“Throughout my career, I’ve always found that it kind of didn’t matter what I was working on, it mattered the person I was working for.”
– Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products at Salesforce

26. Build agents to grow your impact, not your headcount.

“I also think the smart ones will go. This is my opportunity to leapfrog leadership, because I don’t need to hire and build a laBuild agents to grow your impact, not your headcount.rge team to have impact… If someone came to me and said… I don’t need to hire 2 or 3 people. I’ve built these agents, and they’re doing the work of 2 or 3 people or ten people or whatever that is. I am definitely going to promote them and give them more responsibility.”
– Meagen Eisenberg, CMO at Samsara

Fundraising

27. Don’t mistake a VC’s outreach for interest.

“One thing I coach founders on all the time is that a VC reaching out to you, wanting to learn more about your company, does not mean they are interested in investing. They’re simply doing their job to talk to every single company on earth.”
– Ryan Denehy, Founder and CEO at Electric

28. Make investors prove their value before the check.

“Don’t just give me your thesis and your value and your deck… I always say to people, show up consistently and do the work.”
– Elias Torres, Co-founder and CEO at Agency (now CPO at Klaviyo)

29. Get customers live fast, or nothing else matters.

“If you do not get people into the product with appropriate enablement and guidance really quickly and at a really high level, it doesn’t matter what you do.”
– Patrick Forquer, CRO at Legora

30. Hire two post-sale people for every presale hire.

“…I hired 2-to-1 post-sale to presale. So we are… heavily, heavily focused on implementation change management and then ongoing transformation.”
– Patrick Forquer, CRO at Legora

31. Put engineers inside your biggest accounts.

“Having a forward-deployed engineering team… would allow us to increase the usage and satisfaction with our product really, really significantly. And so we did that with two customers, and we just ended up seeing usage grow 5 to 10x immediately… it really is such a game changer for those large enterprise customers.”
– Shensi Ding, Co-founder at Merge

32. Give agents the 90 things your team never gets to.

“As a human, let’s say that you can only do ten things for each customer… But what if we wanted to do another 90 things that we just never had a chance to do for the customer?”
– Elias Torres, Co-founder and CEO at Agency (now CPO at Klaviyo)

33. Go on site with customers more often.

“Getting on site with customers… You can always be doing five times more. And that’s going to be the number one way of moving pipeline, moving revenue, customer expansion, lowering churn.”
– Ross Rich, Co-founder and CEO at Accord

What kept coming up

Read all 33 together and three ideas stand out. AI pays off fastest when the process and data underneath it are already in shape. Speed matters, both in reaching the buyer and in getting them live. And plenty of what moves revenue still happens off the dashboard, like getting on site with customers and being honest when a deal isn’t a fit.

Which of the 33 are you already doing? Let us know in the comments. If one of these landed, the full episode is on YouTube, Apple and Spotify.

Tag @GTMnow so we can see your takeaways and help amplify them.

Workday agreed to acquire C1.ai, an agentic identity platform that manages access rights for both people and AI agents. Agent identity is becoming the adjacency every enterprise software buyer wants – it lands in the same current as the Salesforce/Listen Labs deal and Nvidia’s agent push.

Nvidia is reportedly in talks to acquire or invest in Reflection AI, per the Financial Times. Reflection builds open frontier models, and the talks suggest Nvidia may want its own model lab as the AI stack keeps consolidating.

Nous Research raised $90M at a $1.5B valuation to bring its open-source Hermes Agent to enterprise. Downloaded 24M+ times, driving an estimated 2.5% of global token usage, and on track to hit $100M ARR by year end.

Manus raised $500M+ after China forced Meta to unwind its $2B acquisition. Revenue went from $100M ARR at acquisition to $500M run rate by June — despite the deal falling apart. Back independent, launched 2.0, and now competing directly with Meta’s own Muse agent.

Pluto Security raised $42M to secure enterprise AI agents, automatically mapping every agent across endpoints, cloud, and SaaS before they become a risk. 40+ enterprise customers, 1M+ secured endpoints. The more agents enterprises deploy, the more urgent the governance layer becomes.

Hone raised $60M seed at a $285M valuation, led by Benchmark and Index Ventures, to build AI agents that own business outcomes over weeks or months. Five months old, founded by former OpenAI and Cognition employees. A $60M seed says everything about where enterprise AI investment is heading.

GTM: He Went From Pro Poker to a $100M Exit | George Kurdin, Monk

Listen through the links in the page above or by searching wherever you get your podcasts “The GTMnow Podcast.”

Austin Sensing Company (GTMfund company) – raised $11M seed led by Bow Capital, with GTMfund participating, to build the world’s best sensors and sensor fusion. Since launching this summer, systems are already deployed with 40+ police departments, fire departments, military units, and universities — at wildfires, airports, and with the U.S. military. Manufacturing-first, with a 20,000 sq ft factory in Austin and high-volume production starting next year.

Numeral – raised $100M in Series C funding to expand its AI-powered sales tax and VAT compliance platform. Total capital now sits at $157M, with 3,500+ businesses using Numeral to stay compliant across US sales tax and global VAT. Founder Sam Ross announced the round – linking the company blog since standalone press coverage was thin.

Floqer – is pitching at TechCrunch Disrupt’s Startup Battlefield with $1.2M ARR and roughly 10x revenue growth over the past year. Its AI agents continuously research companies and contacts so B2B sales teams don’t have to – customers report cutting prospecting time by up to 70%. Next move: open-sourcing its autonomous customer knowledge database in early 2027.

Othello – raised $8M in seed funding from a16z speedrun, Owl Capital, and Long Journey Ventures for real-time AI sales coaching. Its in-call model gets live suggestions to reps in under 500 milliseconds while the buyer is still on the line. Customers include Microsoft, Capital One, and Lyft.