How to Sell by Tyler Bosmeny
Y Combinator
52 min, 33 sec
A comprehensive walkthrough on sales strategies for startups, covering the journey from prospecting to closing deals.
Summary
- The speaker discusses the importance of founders mastering sales and the necessary steps for successful sales strategies.
- Prospecting involves finding leads using methods like networking, conferences, and cold emails.
- Conversations should be focused on listening to understand customer needs, which is the core of sales.
- Closing deals includes navigating contract negotiations, avoiding certain traps like free trials, and ensuring commitment.
- The type of sales motion and pricing strategy must align with the startup's product and intended customer base.
Chapter 1
![Introduction to the current week of startup school, highlighting the importance of lectures and the mid-point feedback form.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjAsInB1ciI6ImJsb2JfaWQifX0=--f8d16b4b468d7fe83a0f65b59816d0aed2f62e01/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_33.jpg)
Introduction to the current week of startup school, highlighting the importance of lectures and the mid-point feedback form.
- We are at the midpoint of startup school, a critical time for founders.
- There's an anticipation for talks by Tyler from Clever on sales and Harsh and Amin from Triplebyte on building engineering organizations.
- The speaker emphasizes the value of feedback for the startup school program.
![Introduction to the current week of startup school, highlighting the importance of lectures and the mid-point feedback form.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjAsInB1ciI6ImJsb2JfaWQifX0=--f8d16b4b468d7fe83a0f65b59816d0aed2f62e01/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_33.jpg)
Chapter 2
![The importance of selecting meaningful metrics and providing authentic updates to measure progress.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjQsInB1ciI6ImJsb2JfaWQifX0=--812ac3ff526f59d9ff5fabbd9e7f5e45a1e3c664/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_100.jpg)
The importance of selecting meaningful metrics and providing authentic updates to measure progress.
- Founders should think critically about the metrics they use to track progress.
- It's advised to avoid vanity metrics that don't measure the true road to success.
- Updates should be honest reflections of milestones towards the startup's goals.
![The importance of selecting meaningful metrics and providing authentic updates to measure progress.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjQsInB1ciI6ImJsb2JfaWQifX0=--812ac3ff526f59d9ff5fabbd9e7f5e45a1e3c664/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_100.jpg)
Chapter 3
![Introduction of Tyler Bosmeny, CEO of Clever, who will share insights on sales.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjcsInB1ciI6ImJsb2JfaWQifX0=--ab57c1574b75e0ea4ca7cc2e190c61517d3aad79/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_148.jpg)
Introduction of Tyler Bosmeny, CEO of Clever, who will share insights on sales.
- Tyler Bosmeny is introduced as the CEO of Clever, which is utilized by over half the schools in America.
- He is set to discuss the significance of mastering sales as a founder.
![Introduction of Tyler Bosmeny, CEO of Clever, who will share insights on sales.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNjcsInB1ciI6ImJsb2JfaWQifX0=--ab57c1574b75e0ea4ca7cc2e190c61517d3aad79/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_148.jpg)
Chapter 4
![Tyler Bosmeny recounts his unexpected path to becoming proficient in sales.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNzMsInB1ciI6ImJsb2JfaWQifX0=--950d14213c8fcb8c5c192e87680f23ee9d9e2c00/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_214.jpg)
Tyler Bosmeny recounts his unexpected path to becoming proficient in sales.
- Tyler shares his background in math and statistics, and his initial disinterest in sales.
- He describes his first experience with sales while working on a college newspaper and later joining a startup.
- Tyler emphasizes the unexpected fulfillment found in the sales process and its importance.
![Tyler Bosmeny recounts his unexpected path to becoming proficient in sales.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNzMsInB1ciI6ImJsb2JfaWQifX0=--950d14213c8fcb8c5c192e87680f23ee9d9e2c00/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_214.jpg)
Chapter 5
![Tyler discusses the reality of sales being a core responsibility for founders.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNzgsInB1ciI6ImJsb2JfaWQifX0=--cb138445f8288f59fa926571299714f7b57fc7d9/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_423.jpg)
Tyler discusses the reality of sales being a core responsibility for founders.
- The common misconception of sales being only for charming individuals is dispelled.
- Founders, with their passion and industry expertise, are uniquely positioned to be effective at sales.
- Tyler highlights the importance of founders taking an active role in sales, especially in the early stages of their startups.
![Tyler discusses the reality of sales being a core responsibility for founders.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwNzgsInB1ciI6ImJsb2JfaWQifX0=--cb138445f8288f59fa926571299714f7b57fc7d9/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_423.jpg)
Chapter 6
![Tyler outlines the sales funnel, from prospecting to closing the deal.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwODAsInB1ciI6ImJsb2JfaWQifX0=--2b83f04d925faa11ac4ba6fb1ac08115ce9eb858/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_633.jpg)
Tyler outlines the sales funnel, from prospecting to closing the deal.
- The sales funnel includes finding prospects, having conversations, closing deals, and generating revenue.
- Prospecting requires reaching out to a significant number of potential leads to find interested buyers.
- Tyler shares the importance of persistence and following up throughout the sales process.
![Tyler outlines the sales funnel, from prospecting to closing the deal.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwODAsInB1ciI6ImJsb2JfaWQifX0=--2b83f04d925faa11ac4ba6fb1ac08115ce9eb858/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_633.jpg)
Chapter 7
![Discussing methods for identifying prospects and starting conversations.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwODQsInB1ciI6ImJsb2JfaWQifX0=--471c48993505feeee1aae4d439454b073138d972/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1009.jpg)
Discussing methods for identifying prospects and starting conversations.
- Prospecting methods include using personal networks, attending conferences, and sending cold emails.
- Tyler highlights the effectiveness of conferences in meeting potential customers and encourages thorough preparation.
- Cold emails should be concise, personalized, and aim to initiate a conversation.
![Discussing methods for identifying prospects and starting conversations.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwODQsInB1ciI6ImJsb2JfaWQifX0=--471c48993505feeee1aae4d439454b073138d972/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1009.jpg)
Chapter 8
![Tyler emphasizes the importance of listening in sales conversations.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwOTIsInB1ciI6ImJsb2JfaWQifX0=--cb668062823088fe8b187767b03fb57c97d196a3/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1382.jpg)
Tyler emphasizes the importance of listening in sales conversations.
- Effective salespeople spend more time listening than talking during sales conversations.
- Asking the right questions and genuinely understanding customer problems is key to successful sales.
- Sales is about building relationships and providing solutions, not just pushing a product.
![Tyler emphasizes the importance of listening in sales conversations.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwOTIsInB1ciI6ImJsb2JfaWQifX0=--cb668062823088fe8b187767b03fb57c97d196a3/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1382.jpg)
Chapter 9
![Tips for successfully closing deals and navigating potential pitfalls.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwOTgsInB1ciI6ImJsb2JfaWQifX0=--c0c8f303fd0716a30007013cc7b11fa42ce43a01/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1922.jpg)
Tips for successfully closing deals and navigating potential pitfalls.
- Closing requires having a solid contract, managing negotiations efficiently, and being willing to compromise on non-critical terms.
- Tyler advises against building features for one-off requests, offering free trials, and highlights the need for commitment.
- Being persistent is key, but also knowing when to accept a 'no' can save time for other potential deals.
![Tips for successfully closing deals and navigating potential pitfalls.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAwOTgsInB1ciI6ImJsb2JfaWQifX0=--c0c8f303fd0716a30007013cc7b11fa42ce43a01/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_1922.jpg)
Chapter 10
![Final insights on sales strategies and hiring the right salespeople.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAxMDIsInB1ciI6ImJsb2JfaWQifX0=--575433adb7bfe16a710583675e16324794dabfbb/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_2777.jpg)
Final insights on sales strategies and hiring the right salespeople.
- Founders should consider the long-term sales motion and pricing model for their startups.
- The type of salesperson to hire (Renaissance vs. coin-operated) corresponds to the stage of the startup's journey.
- Tyler concludes by encouraging founders to enjoy the process and wishes them good luck.
![Final insights on sales strategies and hiring the right salespeople.](https://www.videogist.co/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MzAxMDIsInB1ciI6ImJsb2JfaWQifX0=--575433adb7bfe16a710583675e16324794dabfbb/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fbGltaXQiOls3MjAsbnVsbF19LCJwdXIiOiJ2YXJpYXRpb24ifX0=--c9426325207613fdd890ee7713353fad711030c7/2067_2777.jpg)
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