On The Frontier

Jake Saper is a General Partner at Emergence Capital which has backed leading SaaS companies like Salesforce, Zoom, Gusto, Bill.com, and Veeva. Jake is a Board member of companies like Guru, Textio, Ironclad, Maze & many others. When I wanted to do a deep dive into SaaS business models, I could think of no one better than Jake and this episode absolutely delivered. We cover everything from single-player to multi-player product modes, various moats in SaaS, and how SaaS pricing & business models are evolving. We dive into specific anecdotes from companies like Zoom, Guru, Textio and others around how their products scaled. Finally, we end with how AI and LLMs will impact SaaS in the future and how founders should think about using LLMs in their products.

Where to Find Jake:

* Twitter: https://twitter.com/jakesaper

* LinkedIn: https://www.linkedin.com/in/jakesaper/

* Emergence’s Blog: https://www.emcap.com/thoughts

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(01:11) - Learnings from Zoom, Salesforce, Veeva, Gusto & Others

(04:52) - Jake’s Framework for Evaluating Messianic Founders & Lasting Products

(13:05) - Single Player vs Multi-Player Products

(14:53) - Individual Usage vs Viral Adoption in an Org and the Deep Collaboration Thesis

(20:49) - Quick Takes on Net ARR Growth, PLG vs PLS with Zoom as an Example

(25:51) - When and How to Evaluate Moving into Adjacencies (Gusto & Veeva Example)

(34:35) - Moats in SaaS

(38:51) - Role of Community in SaaS

(41:45) - Emergence’s Coaching Network Thesis

(44:28) - LLMs Impact on SaaS & How Founders Can Position Around It

(53:41) - Outcomes Based Pricing in SaaS

(55:09) - How Textio Leveraged Data Hacks to Build a Moat

(59:01) - AI Impact on Software Margins and Honing in on the Value & Job to Be Done

Show Notes:

* How to Hack Your Way Into a Proprietary Dataset

* GenAI’s Impact on SaaS & Founders Building in SaaS

* How to Price AI in SaaS

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Ian Swanson is the Co-Founder & CEO of Protect AI which secures AI and ML systems. He was previously the Co-Founder & CEO of Datascience.com which sold to Oracle, where he was VP AI & ML and then was Worldwide Leader of AI & ML at AWS before starting Protect AI. I’m also joined by Emilio Escobar, CISO of Datadog as a special co-host! In this episode, we dive into what is ML & AI Security, the different types of attacks that hackers are using, and how teams can best secure their systems. We also talk about MLSecOps and why an ML BOM (Bill of Materials) is needed. Finally, we cover emerging attack surfaces and how LLMs will change both adversarial and defensive security products.

Where to Find Ian:

* Twitter: https://twitter.com/ianrswanson

* LinkedIn: https://www.linkedin.com/in/ianswanson/

* Company Website: https://protectai.com/

* MLSecOps Community & Podcast: https://mlsecops.com/

Where to Find Emilio:

* Twitter: https://twitter.com/eaescob

* LinkedIn: https://www.linkedin.com/in/emilioesc/

* Emilio’s Newsletter: https://emilioe.substack.com

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:41) - Ian and Protect AI’s Background

(03:54) - Enteprise Adoption in AI & ML

(07:11) - What is MLSecOps and the Supply Chain Behind AI & ML

(14:23) - ML Poisoning Attacks & New Adversarial Attacks Emerging

(24:01) - State of Enterprise ML Teams and Understanding of Security

(30:46) - Differences Between AI & ML Security

(35:54) - New Attack Surfaces

(43:15) - CISO Viewpoint on How to Manage AI Adoption in an Org

(50:15) - How AI is Advancing Adversarial and Defensive Security Techniques & Tooling

(55:50) - Vision of the Future for What Good AI Security Enables

Show Notes:

* How Electronic Arts Red Teams AI/ML Attack Surfaces

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Jade Rubick is a Eng Advisor to multiple startups (23 and counting). He was previously Vice President Engineering at New Relic and has taken on interim VPE roles at multiple other startups over the years before he began solely focused on advising startups. In this episode, Jade joins us to cover common anti-patterns he sees in eng teams, how teams can better communicate, what hiring practices work well and how to think about structuring career paths for employees. Everything from hiring tips, to product & feature development, to adjusting to the current “do more with less” environment and common advice across all startups is covered in this episode. For anyone interested in learning how to run effective eng orgs, this is the episode for you.

Where to Find Jade:

* Twitter: https://twitter.com/JadeRubick

* LinkedIn: https://www.linkedin.com/in/jaderubick/

* Personal Website and Newsletter: https://www.rubick.com/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:49) - Jade’s Background

(02:57) - When to Hire an Eng Leader & Common Anti-Patterns

(09:47) - Career Paths for Eng Management and IC and How to Identify Who Is a Fit

(17:13) - How Eng Teams Can Best Interface with Other Orgs

(28:41) - Frameworks for Balancing Scalability and Speed with Delivering Product

(34:58) - Adjusting and Operating in a Do More With Less Environment

(39:50) - Common Repeated Advice from Working with 20+ Startups Over Time

Show Notes:

* Playbook for Hiring Eng Managers

* How to Solve Cross Team Priorities

* High Trust and Low Trust Organizations

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Julia Schottenstein is a Product Lead at dbt and an active angel investor. Julia was previously a VC at NEA focused on software and data infrastructure. She joins us today to share learnings from product and VC, why analytics engineering is continuing to proliferate, and how dbt has been able to manage and grow the community over time. We dive into the data transformation and semantic layer and cover how dbt thinks about the open source and cloud products, managing feedback from all users to improve the product. We end with exciting trends for the future of data (hint LLMs are mentioned!).

Where to Find Julia:

* Twitter: https://twitter.com/j_schottenstein

* LinkedIn: https://www.linkedin.com/in/julia-schottenstein-25424318/

* Analytics Engineering Podcast: https://roundup.getdbt.com/s/the-analytics-engineering-podcast

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:34) - Julia’s Background, Running Marathons, & Qatalyst’s Dominance

(06:45) - How dbt Became Not Just a Product But an Identity for Practitioners

(09:14) - What Does dbt Do?

(11:41) - Comparing & Contrasting Software & Data Engineering Practices

(14:01) - How dbt’s Community Started and Has Continued to Grow at Scale

(19:04) - Why dbt is Unlikely to Move into the Visualization/BI Layer

(20:35) - Text to Sql and LLMs Impact on Data Workflows

(23:15) - Why Self Serve Data Assets in Companies is Hard to Achieve

(24:50) - Analytics Engineering Trends

(30:03) - What’s the Deal With the Modern Data Stack Today in It’s Evolution

(32:07) - Transitioning from VC to Product

(35:01) - Balancing OSS and Cloud Products

(39:08) - Managing Rapidly Scaling Orgs

(42:40) - Trends in Data That Julia is Excited About

(44:56) - Favorite Technology and Snack

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Kiersten Gaffney is the Chief Marketing Officer of Codefresh and a Go-To-Market Advisor for AtomicJar, CodeSee, Fermyon, Redis & many more companies. Kiersten was previously a marketing leader at Buoyant and Mesosphere, with many years of experience in software infrastructure and developer tools. She joins us today to share detailed tactics for dev tools founders on how to “do more with less”, designing content strategies, and leveraging communities to propel go-to-market forward. We dive into hiring insights on what marketing personas to hire at what stage and talk about specific tactics that Kiersten employed at previous and current roles to generate qualified leads in the funnel.

Where to Find Kiersten:

* LinkedIn: https://www.linkedin.com/in/kierstengaffney/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:46) - Kiersten’s Background & Ramping Up In the Cloud Native Ecosystem

(03:28) - What Marketing Roles Should Founders Hire For At Each Stage

(06:21) - Events and Speaker Strategies for Early Teams to Leverage

(09:29) - Anecdotes from Mesosphere and CodeFresh

(11:24) - Easy Ways to Create and Sustain a Content Engine

(15:40) - Leveraging Community for GTM

(17:15) - Marketing Tactics for OSS vs Proprietary Companies

(21:50) - The Fallacy of Focusing on Features Instead of Value

(23:00) - How Messaging Changes as Companies Move Up-Market

(26:23) - When to Start Using Account-Based Marketing and Why

(30:45) - How do “Do More With Less” in Marketing

(35:22) - Marketing Tips for Highly Competitive Markets

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Dan Scheinman is a full-time Angel Investor and Board Member of Zoom, SentinelOne, and Arista Networks. He joins us today to share learnings about M&A from his time running Corp Dev at Cisco, backing multiple public companies from day one, and how public boards differ from private ones. There’s numerous anecdotes that Dan shares about how he finds outlier founders, how founders are able to succeed even when they’re building in already competitive markets, and tons of actionable advice for founders today on everything from focus to capital allocation to M&A decisions.

Where to Find Dan:

* LinkedIn: https://www.linkedin.com/in/danscheinman/

* Twitter: https://twitter.com/dscheinm

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:56) - Dan’s Background & Stories About Cisco

(07:28) - How Cisco Was Able to Effectively Execute M&A (59,000% return since IPO)

(11:40) - Tips for When Founders Should Approach and Leverage M&A as an Acquiror

(13:45) - Finding Outlier Founders from Day One

(17:18) - SentinelOne, Zoom, Arista Founders Navigating and Succeeding in Already Crowded Markets

(24:58) - Premature Scaling as the Biggest Risk in Early Startups

(27:52) - Founder Transitions from Private to Public Markets

(31:19) - Balancing Internal & External Comms and Where All Hands Fall Short

(33:25) - Capital Allocation

(38:30) - Being an Effective Board Member

(42:51) - Why Focus is So Essential at the Pre/Early in Product Market Fit Stage

(51:41) - Being a Value Investor in Startups

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Phillip Carter is a Principal Product Manager at Honeycomb, which develops a software debugging product for distributed systems. Phillip recently published one of the most interesting blog posts I’ve read titled “All the Hard Stuff Nobody Talks About when Building Products with LLMs”. The post is excellent and everyone should give it a read. In this episode, we dive deep into what the hard stuff actually is, the pros and cons of Large Language Models (LLMs) and what teams need to think about when using LLMs in their products. We also talk about the real world results that come from shipping an LLM-enabled product, including the conversion increases that Honeycomb has seen as a result of Query Assistant and how the decision to use LLMs came about. For all the teams wondering how to use LLMs now, this is the episode for you.

Where to Find Phillip:

* LinkedIn: https://www.linkedin.com/in/phillip-carter-4714a135/

* Twitter: https://twitter.com/_cartermp

* Personal Website: https://phillipcarter.dev/

* Blog Post Referred to in Podcast: https://www.honeycomb.io/blog/hard-stuff-nobody-talks-about-llm

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:49) - Phillip’s Background and What Honeycomb Does

(06:37) - How the Idea to Use LLMs for the Query Assistant Product Occurred

(08:45) - Managing Context Windows and Token Counting

(14:35) - Few Shot Prompting & Schema Context

(16:32) - The Conversion Results from Using LLMs to Power a New UI

(21:36) - Are LLMs Mainly Useful for Search & UI/UX

(28:09) - Should Companies Have an “AI Strategy”

(31:55) - Best Efforts Results for LLM Output

(36:10) - Managing Direct Database Access for LLMs

(40:51) - How Embeddings Can Help with Context Windows

(44:31) - Guiding UI/UX Principles for LLM Features

(47:52) - The Magic That LLM Features from a UI Perspective Can Provide

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Julian Alvarez is the CEO & Co-Founder of Logixboard, which is enabling freight forwarders to deliver a modern, digital customer experience to their customers with the Logixboard platform. He joins us today to talk about how to understand customer pain points in a specific vertical and gives a detailed overview of the freight forwarding and supply chain industry. Julian covers how to build a vertical SaaS software company, how scaling in vertical SaaS is different from other industries, and what sort of integrations and technology aspects vertical SaaS software companies need to take into account. For any founders, investors, or generally people curious about Vertical SaaS and the supply chain industry, this is the episode for you.

Where to Find Julian:

* LinkedIn: https://www.linkedin.com/in/julian-alvarez-751943126/

* Logixboard Website: https://logixboard.com/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:36) - Julian’s Background & Building in Different Industries

(05:05) - How Julian Learned about the Freight Forwarding Industry

(10:13) - Finding Product Market Fit and Rearchitecting the Product Early

(13:26) - Overview of Supply Chain Industry

(16:32) - Segmentation of the Freight Forwarding Industry

(18:29) - Key Technology in the Freight Forwarding Space & The Visibility Challenge

(20:53) - Enabling Digital Transformation in a Longstanding Industry

(30:00) - Indirect Network Effects in a B2B2C Platform

(34:32) - Customer Density in GTM for Vertical SaaS

(36:39) - Hiring for Vertical SaaS and How to Do Knowledge Enablement

(38:24) - Pros & Cons of Hiring Directly from Industry Expertise

(40:29) - Biggest Challenge of Building a Vertical SaaS Company

(43:51) - What Will a Single Pain of Glass Customer Experience Platform Across the Entire Supply Chain Look Like

(45:33) - Favorite Technology/App

(46:34) - Favorite Snack

Additional Show Notes:

* Customer Stories of How Logixboard Helps Them Win Business

* Specific Freight Forwarding Content from Logixboard

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.

Mia Wang is the M&A & Strategy Director at Cloudflare. Oren Falkowitz is the Co-Founder of Area 1 Security, a phishing security company, which was acquired by Cloudflare in April 2022. In this episode, Mia & Oren demystify the M&A process for startups (founders and employees) by discussing the real steps and decisions that both sides had to make as the acquisition was being contemplated and completed. Tactical advice is shared all along the way for founders to learn from in order to enable the smoothest M&A process possible in the future.

Where to Find Mia:

* LinkedIn: https://www.linkedin.com/in/miaywang/

* Twitter: https://twitter.com/miawang__

Where to Find Oren:

* LinkedIn: https://www.linkedin.com/in/orenjfalkowitz/

* Twitter: https://twitter.com/orenfalkowitz

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:44) - Mia’s Background

(02:24) - Oren’s Background

(05:02) - Quick Primer on Ballistic Missile Trajectories and Telemetry (fun tangent)

(06:57) - How Acquirers Approach the M&A Process

(10:03) - Build vs Acquire Decision

(11:39) - What Area 1 Security Does

(13:42) - Starting a Phishing Security Company in an Already Crowded Market

(15:43) - LLMs Impact on Phishing Security

(18:48) - What Happens At and After the First Exploratory Call

(25:34) - The Research & Initial Diligence Process of an Acquirer

(29:31) - Balancing Regular Business and Acquisition Interest as the Target

(33:43) - Getting to the Actual Price & Valuation

(36:54) - Negotiating Price as the Target & Communicating Internally with Board & Teams and Externally with Customers

(45:14) - Navigating Closing Conditions and Accelerating Delivering the Employees and Talent the Acquirer Expects to Bring Onboard

(46:44) - Post Closing Integration

(51:52) - Key Tip from Acquirer’s Perspective on Making M&A Go Smoothly

(53:43) - Key Tip from Target’s Perspective on Making M&A Go Smoothly

(54:47) - Fun Story on Cultural Fit and How Little Things Matter

Additional Show Notes:

* Why Cloudflare Acquired Area 1 Security

* Cloudflare Completes Acquisition of Area 1 Security

* Area 1 Security Product Page within Cloudflare

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google or any podcast player.

Kyle Poyar is Operating Partner at Openview focused on PLG, pricing & growth. He writes the amazing and widely read newsletter, Growth Unhinged, which is one of my favorite weekly reads (multiple times a week!). It’s a wealth of information and I highly recommend listeners subscribe. Kyle joins us today to dive into all things PLG. He shares detailed and highly actionable tips with real-world examples of the countless startups he’s studied and worked with. We talk about PLG motions, multiplayer vs single-player, pricing & packaging, marketing tactics, retention and more. We could have gone on for much longer and may have to do a follow-up in the future. This episode is frankly helpful for anyone, founders, startup employees, customers, and investors both public and private.

Where to Find Kyle:

* LinkedIn: https://www.linkedin.com/in/kyle-poyar/

* Twitter: https://twitter.com/poyark

* Growth Unhinged Newsletter: https://kylepoyar.substack.com

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Newsletter: https://www.shomik.substack.com

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:35) - Kyle’s Background

(01:49) - What is Product Led Growth

(03:22) - Where Founders Should Start to Truly Do PLG

(06:58) - Case Studies of Companies That Have Transitioned to PLG Over Time

(08:54) - Self Serve Onboarding vs Self Serve Pricing and How They Affect PLG

(11:17) - Single Player vs Multi-Player Product Models Mapping to PLG

(14:59) - Pricing for Different Product Models

(18:34) - Why Being “Generous” with a Seat-Based Pricing Model Can Be Highly Effective (Canva Case Study)

(21:13) - What Are Reverse Free Trials

(24:25) - How Can Reverse Free Trials Fail

(26:25) - What is Product Led Sales

(30:27) - Sales-Assist as a GTM Model

(33:53) - Product Led Marketing

(40:25) - Product Evangelists in SaaS

(46:24) - Managing Churn & Retention Between Different Product Models

(49:48) - Seat Based vs Usage Based Pricing

(52:24) - How Hybrid Pricing Models are Increasing in Prevalence

(55:11) - Sequencing the Various Steps to Get to a PLG Motion

Additional Show Notes:

* How to Optimize Your Free Trial

* Guide to Product Led Sales

* Guide to Product Led Marketing

* Openview’s Mastermind Community for PLG Insights

How to Subscribe:

Available on Apple Podcasts, Spotify, or Google.