#64 How to create & execute a killer plan - “Plan the Work, Work the Plan”

Today we unpack how you can apply systems thinking in your startup and build high-value 'systems. You get the three-question framework for mapping workflows, cutting noise, and focusing on the high-value steps and how we've applied it at Zipline.io!The few chaptersDefining a “system” and why complexity naturally creeps inMapping your core workflows as “arteries” and spotting the noisy “capillaries”The three essential questions to evaluate any process:What’s the goal?How frequently does it run?How much waste or risk is in the flow?Real-world examples in recruitment and finance on pruning unnecessary stepsPractical tactics for trimming complexity and building lean, scalable operationsConnect with Us:Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠)Zabi Rawan (linkedin.com/in/zabi-rawan)📣 Feedback, ideas or career questions? Send us an email - [email protected]

In our first mini book club, we unpack Peter Drucker’s timeless book "The Effective Executive" and how you can bring it to life in your world. Some basics: Tracking exactly where your time goesZeroing in on outcomes over tasksDoubling down on strengthsHoning in on the few priorities that drive outsized results.Along the way, we share real Zipline stories on time-blocking, weekly accountability rhythms, and the mental habits that keep our “monkey brain” in check. What we want you to really get out of this is effectiveness can be learned - it's not some trait people inherit.

Sales has become a dirty word—known for aggressive tactics, high-pressure targets, and customer frustration. MM and Zabi sit down to talk through why this doesn’t work, especially in B2B SaaS.We share exactly what great sales looks like: genuine problem-solving, aligning closely with customer pain, and building real relationships. How Zipline built a strong sales culture, deep product<>sales collaboration, why hiring for culture matters, how product agility makes selling easier, and why we believe in rewarding high performers generously.If you’re tired of traditional sales or curious how a startup like Zipline actually makes sales enjoyable and effective, listen in.P.S. Yes we're hiring for sales role right now! If this resonated, reach out!-- Check out our latest roles: https://www.linkedin.com/company/zipline-io/posts/?feedView=allConnect with Us:Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠)Zabi Rawan (linkedin.com/in/zabi-rawan)📣 Feedback, ideas or career questions? Send us an email - [email protected]

We're back! Maddie's left for Ireland 🇮🇪 for new adventures and we've been working in the background on a refresh as Zabi comes on board!In this episode we cover what inspired the rebrand (hint: we're seeking growth at Zipline!) who is this for and what you can expect over the coming months. SynopsisThe rebrand was inspired by Zipline, our startup gearing up to scale up. With this refocus, our thinking and questioning has shifted away from raw startup career advice to broader lessons learnt by Mike and the team.We want ambitious individual contributors, aspirational execs and founders to go "💡ahh yeh that makes so much sense".We'll focus on 3 areas throughout the poddyOur current thinking (and lessons learnt) on all things scale-ups Reflections on the past; what we did, why and how our thinking has evolvedCoaching and mentorship; how to approach 1:1s; how to write briefs to executives and the psychology of the modern-day knowledge worker. -- Check out our latest roles: https://www.linkedin.com/company/zipline-io/posts/?feedView=allConnect with Us:Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠)Zabi Rawan (linkedin.com/in/zabi-rawan)📣 Feedback, ideas or career questions? Send us an email - [email protected]

We've all got some level of perfectionism in us which leads us to trying to optimise everything. In this episode we chat about how to "cook just right" anything you work on - How to identify when you're over optimising - How to prioritise the right things to optimise for - How to think through the tension of high quality and realistic effort

MM regularly gets asked 'What is it truly like to work at Zipline? How would you describe the culture?' In this episode we unpack exactly what it's like to work at Zipline ⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/3KwIiBZ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Connect with Us: Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Maddie Stillman (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/maddie-stillman)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 📣 Feedback, ideas or career questions? Send us an email - [email protected]

In this episode we consider what the smoke signals could be for someone working in a larger organisation who are looking for something more in their day-to-day. If you’re feeling any of these we think you could be very well suited to a career in a startup! Michael’s 5 signals that you should be looking out for (& if you have all 5, it’s time to get in touch with us!): 1. Does the treadmill speed of the organisation match yours? 2. Is the work pulling you in? (would you use any of your spare time to think about work related stuff?) 3. Are you inspired by those 3-5 yrs more senior than you? 4. Are your colleagues people you want to hang out with in 3-5 years time? 5. If you fast forward 3 years time & where you are likely to be, does that excite you? ⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/3KwIiBZ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Connect with Us: Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Maddie Stillman (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/maddie-stillman)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 📣 Feedback, ideas or career questions? Send us an email - [email protected]

In this episode we discuss how staying in your comfort zone and avoiding risk prevents you from finding hyper growth, both personally & professionally. StartUps are a great environment to push yourself out of your comfort zone and embrace discomfort. ⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/3KwIiBZ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Connect with Us: Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Maddie Stillman (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/maddie-stillman)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 📣 Feedback, ideas or career questions? Send us an email - [email protected]

In this episode, special guest Tanmay (Chief Product Officer @ Zipline) runs us through his tried and tested approach to working backwards from an objective/key result to create a plan to execute. First we unpack solution design and then wrap up the episode with project planning. + special insight into the common mistakes Tanmay has seen & why people often fail in achieving their desired outcome. ⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/3KwIiBZ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Connect with Us: Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Maddie Stillman (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/maddie-stillman)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 📣 Feedback, ideas or career questions? Send us an email - [email protected]

⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bit.ly/3KwIiBZ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Connect with Us: Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠) Maddie Stillman (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/maddie-stillman)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 📣 Feedback, ideas or career questions? Send us an email - [email protected]