
Startup Field Guide by Unusual Ventures: The Product Market Fit Podcast
Every overnight success in the world of software happens after years of hard work finding product-market fit. The Unusual Ventures Startup Field Guide is a podcast for early-stage software leaders and aspiring founders looking for help going from 0 to 1. Featuring great conversations with successful startup founders, you will learn about hiring, product research, go-to-market, fundraising, and more.
Latest episodes

Mar 19, 2025 • 30min
Jyoti Bansal on how Traceable found product-market fit
Jyoti Bansal, CEO of Harnessio and TraceableAI, and co-founder of Unusual Ventures, shares his journey in software entrepreneurship alongside his long-time friend John Vrionis. They delve into the recent merger of Harness and Traceable aimed at revolutionizing the DevSecOps landscape. Jyoti reveals the insights that founded Traceable and emphasizes the iterative nature of achieving product-market fit. He offers valuable advice for early-stage founders, stressing the importance of customer discovery and resilience in building successful companies.

7 snips
Sep 15, 2024 • 47min
Samantha Mckenna on why solving customer problems is the best sales strategy
Samantha Mckenna is the founder of SamSales and a leader in building go-to-market strategies. She has spent her nearly 15+ year career in enterprise sales doing two things: breaking over 13 sales records and doing so by leading with a buyer-first approach to sales.
In this episode of the Startup Field Guide podcast, she shares why early stage founders should focus on solving challenges for buyers rather than selling, the need for thorough research and personalization in outbound prospecting, and the effectiveness of LinkedIn as a marketing platform.
Some topics we covered with Sam include:
00:00 Preview: Importance of solving customer challenges first
00:18 Sam’s early journey into sales and GTM
02:20 Common mistakes in enterprise sales process for startups
02:37 Challenges and misconceptions about enterprise sales
04:10 How technical founders can get started in sales
9:26: How founders can start doing outbound sales while building their product
14:26 Tips for effective outbound messaging
18:18 Selling to engineers
19:57 Why founders should be using LinkedIn
22:25: Strategies for marketing on LinkedIn
38:15 AI tools for outbound sales and marketing
43:01 Hiring the right sales leaders for early stage startups
Samantha Mckenna is the founder and CEO of SamSales.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

Aug 25, 2024 • 40min
Relyance AI CEO Abhi Sharma on building an unreasonably hospitable sales culture
Relyance AI is a global privacy compliance and data governance platform that allows enterprises to protect customer data, avoid expensive fines, and build customer trust. It provides visibility and control over all enterprise data processing. In this episode, we chat with Abhi Sharma, CEO and co-founder of Relyance about the early days of the company, and how Relyance has recently completely transformed its sales culture.
Join us as we discuss:
00:00 Preview: Culture is about what you do day-to-day
1:28 The insight behind Relyance
6:20 Early feedback from design partners
9:17 Abhi’s learnings as a second-time founder
11:10 Transforming Relyance’s sales culture and strategy
15:30 How Unreasonable Hospitality influence Abhi’s thinking about company culture
18:18 What the hospitality industry can teach software founders
24:18 How Abhi coached his team into changing their mindsets
30:06 How Relyance’s customers and team have responded to the shift in the sales culture
35:51 Advice for early-stage founders on building strong company culture
Abhi Sharma is the CEO and co-founder of Relyance.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

Jun 28, 2024 • 40min
Clay CEO Kareem Amin on AI-powered outreach for growth
Clay is an AI-powered platform for sales prospecting that gathers data from over 75 sources to build lists and help growth teams send personalized outreach messages. Recently valued at over $500M, Clay has several high-profile enterprise customers, including go-to-market teams at Intercom, Ramp, Notion, Anthropic, Verkada, Vanta, and more.
In this episode, Sandhya Hegde chats with Kareem Amin, CEO and co-founder of Clay.
Join us as we discuss:
00:00 Preview: Picking the right customer
1:53 Lessons learned from Kareem’s first startup, Frame
4:54 Decision behind choosing acquisition for Frame
7:10 The founding insight behind Clay
9:20 Fundraising for Clay
11:52 Narrowing down the ICP for Clay
17:21 Clay’s decision to focus on growth marketers
21:12 Product feedback from early adopters
22:27 Picking the right strategy to monetize
28:37 Building the early team
32:14 Integrating GPT-3 into the product
34:38 Clay’s product roadmap
37:00 Advice for new founders
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc.
Kareem Amin is the CEO and co-founder of Clay.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

Jun 2, 2024 • 28min
Scribe CEO Jennifer Smith on documenting workflows
Scribe makes it easy to share how you do your work by creating automated documentation. Scribe raised a Series B recently and has grown to millions of users with enterprise customers like Gong, LinkedIn, and Shopify.
In this episode, Scribe’s co-founder and CEO, Jennifer Smith chats with Sandhya Hegde about Scribe’s early days.
Join us as we discuss:
00:00 Preview — capturing institutional knowledge
1:46 The insight for starting scribe
5:40 Building the Founding Team
8:10 Product Launch and Early Adopters
12:40 Launching the GA Product
15:08 Analyzing User Feedback and Customer Profiles
16:42 Early go-to-market strategy
20:18 The evolution of Scribe’s GTM strategy
22:50 Leveraging AI
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc.
Jennifer Smith is the CEO and co-founder of Scribe.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

May 19, 2024 • 37min
Eightfold AI CEO Ashutosh Garg on managing talent with AI
Eightfold AI is a talent management platform used by hundreds of large organizations like Vodafone and Activision Blizzard. It helps them leverage data to find great people with the skills they need, both internally and externally. Last valued at $2.1 billion, Eightfold was launched in 2016.
In this episode, Sandhya Hegde chats with Ashutosh Garg, co-founder and CEO of Eightfold AI.
Join us as we discuss:
00:00 Why Ashustosh wanted to build a talent platform
1:47 Ashutosh Garg's early career at Google
5:09 The founding insight for Eightfold AI
7:38 Why Ashustosh decided to focus on HR tech
9:42 Challenges of selling to large enterprises
17:11 Advantages of being an "outsider" in HR tech
19:32 Ashutosh's learnings as a repeat founder
22:58 The impact of recent macro shifts on the labor market
24:50 The impact of GenAI on Eightfold's roadmap
30:16 The future of work
35:11 Advice for first-time founders
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc.
Ashustosh Garg is the CEO and co-founder of Eightfold AI.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

May 5, 2024 • 39min
Monte Carlo CEO Barr Moses on data reliability
Monte Carlo is an end-to-end data observability platform that monitors pipelines for missing or inaccurate data. Last valued at $1.6B, Monte Carlo has over 150 customers, including data teams at companies such as CNN, JetBlue, Hubspot, PepsiCo, and Toast.
In this episode, Sandhya Hegde chats with Barr Moses, co-founder and CEO of Monte Carlo.
Join us as we discuss:
00:00 Preview —Early feedback from a potential customer
1:37 Why Barr and Lior decided to focus on data observability
6:28 Profile of Monte Carlo’s early adopters
12:27 Common pain points among early adopters
16:05 How Monte Carlo narrowed in on their ICP
21: 33 Early product feedback and surprises
26:27 Monte Carlo’s current go-to-market strategy
31:22 How AI will impact the data ecosystem
35:57 Advice for founder building data platforms
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc.
Barr Moses is the founder and CEO of Monte Carlo
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.

Apr 21, 2024 • 35min
Perplexity CTO Denis Yarats on AI-powered search
CTO Denis Yarats of Perplexity, an AI-powered search engine, discusses the company's journey from prototype to 10M users. Topics include text-to-SQL tool, ChatGPT, user data focus, early adopters, core technical competencies, subscription pricing, hardware partnerships, and future product vision. Sandhya Hegde of Unusual Ventures guides the conversation with insights on founder advice in the AI space.

Apr 7, 2024 • 40min
Everlaw CEO AJ Shankar on how AI is accelerating legal tech
AJ Shankar, CEO of Everlaw, discusses the challenges and successes of building a legal tech company, the impact of AI on the legal industry, fundraising hurdles, and the future of Everlaw. Sandhya Hegde explores AJ's journey, technical skills, and evolution as a founder. The podcast offers insights into the intersection of technology and law, highlighting the potential of AI in revolutionizing legal workflows.

Mar 24, 2024 • 41min
Deepgram's CEO Scott Stephenson on Speech AI
Deepgram is a voice AI company that has built an incredible reputation in the market for the quality of its speech recognition. Last valued at over $250M, Deepgram has over 500 customers, including NASA, Spotify, and Twilio.
In this episode, Sandhya Hegde chats with Scott Stephenson, CEO and co-founder of Deepgram.
Join us as we discuss:
00:00 Preview: Fully contextualized speech-to-speech is the future
01:07 Scott's background in particle physics and starting Deepgram
7:18 Scott's first years as a founder
13:17 How the Deepgram team gathered early customer feedback
17:38 Early use cases and product feedback
22:58 How conversational AI will impact the customer support industry
26:54 Specialized hardware in the AI Industry
30:34 How additional hardware specialization will impact Deepgram
32:14 Deepgram's product vision
36:46 Advice for Founders starting an AI company
Sandhya Hegde is a General Partner at Unusual Ventures, leading investments in modern SaaS companies with a focus on AI. Previously an early executive at Amplitude, Sandhya is a product-led growth (PLG) coach and mentor. She can be reached at sandhya@unusual.vc.
Scott Stephenson is the CEO and co-founder of Deepgram.
Unusual Ventures is a seed-stage venture capital firm designed from the ground up to give a distinct advantage to founders building the next generation of software companies. Unusual has invested in category-defining companies like Webflow, Arctic Wolf Networks, Carta, Robinhood, and Harness. Learn more about us at https://www.unusual.vc/.
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.