SaaStr 779: 5 Things That Are Actually Working and 5 Things That Aren't in B2B SaaS AI with Ironclad's CEO and a16z
Ironclad CEO and co-founder Jason Boehmig joined Seema Amble, Partner at Andreessen Horowitz at SaaStr Annual to share their observations on what's currently working – and what's not quite there yet – for Artificial Intelligence (AI) in SaaS. With Ironclad's journey from an AI-first concept in 2014 to a Series E+ company and a16z's extensive portfolio view, their insights offer a valuable perspective on the current state of AI in SaaS.
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SaaStr hosts the largest SaaS community events on the planet.
Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.
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This episode is sponsored by: Anrok
A question for SaaS finance leaders, do you know where your customers are? Anrok tracks where your sales are creating exposure, and automates tax calculation and filing worldwide. Built for high-growth software companies, Anrok protects your revenue and saves you time. Visit anrok.com/saastr to learn more.
About Alex
Alex Su is a lawyer who's currently the Head of Community Development at Ironclad, the #1 contract lifecycle management technology company that's backed by Accel, Sequoia, Y Combinator, and other leading investors. Prior to joining Ironclad, Alex sold cloud software to legal departments and law firms on behalf of early stage startups. Alex maintains an active presence on social media, with over 180,000 followers across Twitter, LinkedIn, Instagram, and TikTok.
Links Referenced:
Ironclad: https://ironcladapp.com/
LinkedIn: https://www.linkedin.com/in/alexander-su/
Twitter: https://twitter.com/heyitsalexsu
Instagram: https://www.instagram.com/heyitsalexsu/
TikTok: https://www.tiktok.com/@legaltechbro
Leyla Seka has a clear idea of “what makes me great” as the COO of Ironclad: She’s incredibly direct with her team. Although many people are not comfortable with getting direct feedback, she says, “I can’t do my job if I can’t tell you what I’m seeing.” And in the end, she sees her job as one of seeking out the truth, to make her business better.
In this episode, Leyla and Joubin discuss developing peccadilloes as you get older, why a former boss told her “if you’re in a bad mood, don’t come to work,” what a COO actually does for her team, working through the first dotcom bust, why Leyla doesn’t think she’s better than anyone else, the long battle for equal pay, the “victim mindset” in the tech industry, empowering others who don’t have confidence in themselves, and why you can’t outwork every problem.
In this episode, we cover:
Maintaining a positive attitude, and dealing with low-energy days (07:57)
“The culture of the company is why you stay” (12:02)
Overthinking things, good communication and letting go of anxieties (17:50)
Leyla’s previous jobs and her parents’ unusual careers (24:55)
Keeping ego out of it and focusing on the “next best action” (31:10)
Fighting for equal pay for women at Salesforce (39:19)
The double-edged sword of innovation at Salesforce (49:19)
How Leyla makes stars out of the underestimated people on her teams (55:40)
Leaving Salesforce and starting Operator Collective (59:55)
How she started working at Ironclad, and what the company does for customers (01:04:19)
The biggest challenge Leyla has faced in her first six months at Ironclad (01:08:36)
Links:
Connect with LeylaTwitter
LinkedIn
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
Today we deep dive into what startups can learn from the large SaaS incumbents of today.
Sara Varni: CMO @ Twilio on her biggest takeaways from her time at Salesforce.
Erica Schultz: President of Field Operations @ Confluent on her biggest takeaways from her time at Oracle.
Whitney Bouck: COO @ Hellosign on her biggest takeaways from her time at Box.
Leyla Seka: Partner @ Operator Collective on her biggest takeaways from her time at Salesforce.
Ryan Bonnici: CMO @ G2 on his biggest takeaways from his time at Salesforce.
Ryan Barretto: SVP @ Sprout Social on his biggest takeaways from his time at Salesforce
Tien Tzuo: Founder & CEO @ Zuora on his biggest takeaways from his time at Salesforce.
Paul Albright: Board member @ Clarizen on his biggest takeaways from his time at SuccessFactors.
Jaleh Rezaei: Founder & CEO @ Mutiny on her biggest takeaways from her time at Gusto.
Eugenio Pace: Founder & CEO @ Auth0 on his biggest takeaways from his time at Microsoft.
Liat Bycel: VP @ Airtable on her biggest takeaways from her time at Twitter.
Mark Goldberg: Partner @ Index on his biggest takeaways from his time at Dropbox.
Read the full transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.
In Today's Episode You Will Learn:
1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?
2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?
3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?
4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?
Items Mentioned In Today's Show:
Jason's Fave Book: Meditations by Marcus Aurelius
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce.
Missed the session? Here's what Molly and Leyla talk about:
Building a community of allies and allyship
How to drive equality
What you can be doing as an employee to help drive the culture you want
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
SaaStr
Molly Ford
Leyla Seka
Leyla Seka is the executive vice president of the Salesforce Mobile platform experience. Over Leyla's incredible 11 year journey with Salesforce she has seen the team scale from 1,800 to over 40,000 and revenue scale from $500m to over $16Bn. In Leyla's role today, she leads the charge on extending the power of Salesforce with a full portfolio of mobile apps, and is responsible for driving product, go-to-market and other key programs around Salesforce's mobile offerings. Prior to her current role, Leyla was executive vice president of the Salesforce AppExchange, where she launched a refreshed AppExchange storefront, a new partner program, and built an entire AppExchange-focused team, resulting in more than 4,000 solutions, installed nearly 6 million times. Beyond her day-to-day role, Leyla is also the executive sponsor of BOLDforce, Salesforce's organization for expanding and empowering the black community at Salesforce.
In Today's Episode We Discuss:
How Leyla made her way into the world of SaaS with Salesforce when it had 1,800 people and $500m in revenue?
What were Leyla's biggest learnings on people and business model through seeing the first hand hyper-scaling of Salesforce from $500m to $16Bn? How did Leyla evolve and scale as a leader herself in those 11 years? What advice does Leyla give to young people considering whether to found a startup, join a startup or join a hyper-growth company?
Where do things start to break in the scaling of SaaS companies? What needs to be put in place to prepare for hyper-scale? What are the commonalities of where many founders go wrong in the scaling process?
What does Leyla mean when she says, "growing up in product, you have to lead through influence"? How does Leyla think this influence can be created and maintained? How does Leyla think about the balance between effective influence and excessive influence?
Why does Leyla believe that, "you can teach skills but you cannot teach empathy"? What have been her learnings from scaling teams when it comes to hiring and detecting candidates with true empathy? What can one do to nurture that empathy in the culture of the company?
60 Second SaaStr:
What does Leyla know now that she wishes she had known at the beginning?
What is the hardest element of Leyla's role at Salesforce today?
What does Leyla believe in SaaS that most around her disbelieve?
Read the full transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Leyla Seka
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