Navigating Founder-Led Sales: Early vs. Late-Stage Strategies

Jen Abel is the co-founder of JJELLYFISH, where she and her team have worked with over 300 early-stage founders to learn how to sell, do early customer discovery, and set up a repeatable sales motion on the way to their first $1M ARR. In our conversation, Jen shares:

• Why founder-led sales is so crucial early on

• The sales process, step by step

• How to craft effective outreach messages

• Where to find leads

• What three channels work best for outreach

• What to say on your first call

• How to maintain momentum

• Strategies for navigating procurement and closing deals

• Common pitfalls in the sales process and how to avoid them

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Find the transcript at: https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

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Where to find Jen Abel:

• X: https://x.com/jjen_abel

• LinkedIn: https://www.linkedin.com/in/earlystagesale

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Jen’s background

(02:20) The importance of founder-led sales

(08:24) The steps of a sales cycle

(12:01) Tactics for effective cold outreach

(16:47) Conversion rate vs. win rate

(20:20) The time it takes to find product-market fit

(23:06) Identifying and engaging prospects

(30:58) Nailing the first phone call

(34:14) Buying vs. selling

(38:08) Testing the questions to ask

(41:57) Avoiding common sales questions and securing the second call

(43:08) Co-authoring with customers

(45:06) Time-boxing service contracts

(49:20) Why you should avoid demos on the first call

(51:05) Dealing with procurement

(54:22) The power of enterprise sales

(58:14) Getting a signature

(01:00:15) Choosing a focus and overcoming sales challenges

(01:02:19) General timelines

(01:04:27) Final thoughts and advice

(01:13:32) Working with Jen

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Referenced:

• Wiz: https://www.wiz.io/

• JJELLYFISH: https://www.jjellyfish.com/

• Clay: https://www.clay.com/

• A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit

• Airtable: https://www.airtable.com/

• Figma: https://www.figma.com/

• GitHub: https://github.com/

• Vanta: https://www.vanta.com/

• Christine Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/

• Glengarry Glen Ross: https://www.imdb.com/title/tt0104348/

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand-ebook/dp/B0CHY6BNDN

• Sprig: https://sprig.com/

• Zip: https://zip.co/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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