This Week's Episode: In this week's episode, Kevin and Matt sit down with industry leader, Janet Jaiswal, CMO and Global VP of Marketing at Blueshift, to explore the evolving landscape of software sales and marketing. They discuss the importance of storytelling, empathy, and understanding customer pain points to differentiate in a crowded market. Janet emphasizes the need for collaboration between marketing and sales, the significance of win-loss analysis, and the value of building trust with customers. The conversation also touches on the challenges faced by newcomers in the industry and the importance of mentorship and continuous learning.

About Our Guest - Janet Jaiswal:

Janet Jaiswal Janet Jaiswal has spent 20+ years in senior marketing roles at private and public companies such as eBay, Paypal, and IBM Tealeaf. She is currently the CMO / Global VP of Marketing at Blueshift, a San Francisco-based company that helps brands automate and personalize engagement across every marketing channel.
Janet is an advisor with Peakspan Capital and has been recognized as a Top 101 B2B Marketing Influencer by CMO Huddles, a FINITE Top 30 SaaS marketer, and one of the Top 14 Marketers to Watch by Drift. Janet earned a bachelor's degree from UC Berkeley and an MBA at the Tepper School of Business at Carnegie Mellon University.

How to Find out More About Janet Jaiswal:

You can find Janet's profile on LinkedIn:

https://www.linkedin.com/in/janetjaiswal/

Chapters

00:00 Introduction to Software Sales Simplified

01:16 Meet Janet Jaiswal: Insights from a Marketing Leader

02:50 Standing Out in a Crowded Market

05:21 The Evolution of Marketing Messaging

07:39 The Role of Marketing in Sales Enablement

08:47 Testing and Adapting Sales Strategies

11:29 The Art of Storytelling in Sales

13:39 Building Trust and Empathy with Customers

16:27 Rethinking Demo Strategies

18:45 Addressing Customer Skepticism

20:33 Balancing Aspirations with Reality

22:10 Navigating Early-Stage Development Challenges

23:53 The Importance of Post-Mortem Analysis

25:26 Learning from Losses

28:16 Validating Value Propositions

31:15 Advice for Aspiring Marketers

38:08 Farewell - Like, Follow, Subscribe and Comment!

About Software Sales Simplified:

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Why Listen to Software Sales Simplified?

Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.

Copyrighted Broadcast:

Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.