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 chapters

• Mapping your core workflows as “arteries” and spotting the noisy “capillaries”

• The three essential questions to evaluate any process:

  1. What’s the goal?

  2. How frequently does it run?

  3. How much waste or risk is in the flow?

• Real-world examples in recruitment and finance on pruning unnecessary steps

• Practical tactics for trimming complexity and building lean, scalable operations

Connect with Us:

Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠)

Zabi Rawan (linkedin.com/in/zabi-rawan)

📣 Feedback, ideas or career questions? Send us an email - zabi.rawan@zipline.io

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 goes
• Zeroing in on outcomes over tasks
• Doubling down on strengths
• Honing 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.

Have you heard of the 6 critical questions...

1. Why do we exist?

2. How do we behave?

3. What do we do?

4. How will we succeed?

5. What is most important, right now?

6. Who must do what?

In this episode we discuss why working for a company that regular discusses these questions is so important. Kai is back on the pod to share his learnings on this topic from a 500+ person organisation

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⚡️ 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 - maddie@zipline.io

Building your mental toughness is an ongoing journey. When personal/professional setbacks arise and demotivate or distract you in can be hard to get back into a productive mode. In this episode we discuss how to accept the setback & process it to snap back like a rubber band.

Michael steps us through focussing on what you can control, taking a growth mindset, reminding yourself of perspective, find energy giving activities, sticking to routines and reminding yourself of the reasons you're doing these hard things.

—

⚡️ 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 - maddie@zipline.io

In this episode Michael shares his 7 point plan to receive any bad news with confidence:

1. Be a PRO (not an amateur)..

2. Make them feel safe

3. Get clarity- so you can think like Eisenhower

4. Plan the plan

5. Make it about them (show you care)

6. Agree to the check in to “work the plan"

7. Get them to capture actions/plan in writing

Bonus tip #8: Buy time to get cool yourself if required

—

⚡️ 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 - maddie@zipline.io

In this episode Michael shares has 7 point plan to share any bad news with confidence:

1. Prepare and reflect

2. Start with clarity and be vulnerable throughout

3. Be upfront with what you need from them

4. Use facts and specifics

5. Express accountability and responsibility throughout

6. Focus on solutions and next steps

7. Practice active listening

—

⚡️ 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 - maddie@zipline.io

It's never easy to share bad news, but sitting on it or avoiding it is not the answer. In this episode we discuss why this is so important for your areas of responsibility, the different types of bad news & how to spot it.

—

⚡️ 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 - maddie@zipline.io

—

⚡️ 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 - maddie@zipline.io

At Zipline we talk about 's-curve growth,' the journey that takes you from novice to high growth, high growth to master. In this episode we unpack the approach to seeking feedback and coaching (including criticism) to fast track this growth journey.

—

⚡️ 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 - maddie@zipline.io

Part 2 - time to execute on your reflections!

It might feel indulgent to get away from your busy to-do list to spend some time reflecting but this is where true growth can start. In this episode we unpack how step away from busy work and lean into deep thinking and journalling.

—

⚡️ 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 - maddie@zipline.io

It might feel indulgent to get away from your busy to-do list to spend some time reflecting but this is where true growth can start. In this episode we unpack how step away from busy work and lean into deep thinking and journalling.

—

⚡️ 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 - maddie@zipline.io

We call this a 🪃 boomerang request - use this trick to most effectively get input, feedback or approval for your work. Plus if the request expires, you are empowered to execute!

—

⚡️ 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 - maddie@zipline.io

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=all

Connect with Us:

Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠⁠)

Zabi Rawan (linkedin.com/in/zabi-rawan)

📣 Feedback, ideas or career questions? Send us an email - zabi.rawan@zipline.io

A meeting/customer brief serves many purposes: it prepares the meeting host, it forces you to distill your thoughts & succinctly define what the goal of the meeting. Always remember bad prep = bad meeting, good prep = good meeting.

—

⚡️ 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 - maddie@zipline.io

An angry customer or mismatched expectations can certainly trigger your cortisol. In this episode we cover some strategies for how to take ownership, empathise to their situation and take action to work through a plan to rectify.

—

⚡️ 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 - maddie@zipline.io

Reporting directly into an executive leader can look very different on a week to week basis. Maddie & Michael unpack how sometimes you may feel micromanaged and highly scrutinised and other weeks you may barely hear from your boss.

—

⚡️ 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 - maddie@zipline.io

In this episode, we explain ACE (from Winning by Design) - the three steps to kick off a customer meeting:

1. Appreciate your time

2. Check time

3. Expectations / end goal

It might sound simple but getting these 3 steps right is vital to running a successful meeting. Maddie role plays her ACE and gets some gems of feedback from Michael.

—

⚡️ 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 - maddie@zipline.io

You can't expect to nail a meeting if you haven't done the prep. In this episode we unpack how to run an excellent customer meeting.

Often people will over optimise what they want the customer to know. Focusing on what you need them to DO is the single most important thing.

—

⚡️ 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 - maddie@zipline.io

When sending cold email outreach do you consider what the receiver needs to know, how you're making them feel and most importantly have you made it clear what they need to do?

—

⚡️ 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 - maddie@zipline.io

Michael shares additional flavour to Pt 1 of this conversation about radical transparency.

—

⚡️ 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 - maddie@zipline.io

Dive into the concept of radical transparency with us. What is it? How does it show up in the workplace? How does it flow both up (to managers), down (to direct reports) and laterally (to peers). + how Zipline has implemented as a foundational part of our culture.

—

⚡️ 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 - maddie@zipline.io

In this episode we unpack what it means to have an ownership mindset towards your career. How can you set and achieve the right career goals to get where you want to be? To put this into practice we share practical tips to implement continuous self improvement and hold yourself accountable.

—

⚡️ 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 - maddie@zipline.io

Kai is passing the co-host role to Maddie as he steps away from Zipline. Maddie & Kai share their approaches to making bold side steps in their early careers over chasing a linear promotion pathway that is often termed as 'successful.' We talk about the pros and cons of this approach.

—

⚡️ 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 - maddie@zipline.io

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.

Synopsis

• The 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 poddy

1. Our current thinking (and lessons learnt) on all things scale-ups
2. Reflections on the past; what we did, why and how our thinking has evolved
3. Coaching 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=all

Connect with Us:

Michael Momsen (⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠⁠)

Zabi Rawan (linkedin.com/in/zabi-rawan)

📣 Feedback, ideas or career questions? Send us an email - zabi.rawan@zipline.io

Michael shares a story from his telco days early in his career. He knew he would never be the most commercial savvy, so he became an EXPERT on the technicalities of the product.

—

We mentioned:

- Justin Lipman's interview (https://www.evp.com.au/team/justin-lipman)

—

⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

We talk about DHH's post on 'unreasonable urgency', how startups continually need to inject risk, and how that pace setting can come from folks other than the founder.

—

We mentioned:

- DHH article (https://world.hey.com/dhh/don-t-lose-your-unreasonable-sense-of-urgency-b381699c)

—

⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

So you're handing in your resignation. Or perhaps being made redundant (Step 1: Be unlayoffable). In this ep, we talk about how to be a "good leaver" in those final days and weeks, and leave the lasting impression you want going into your next career chapter.

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⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠https://bit.ly/3KwIiBZ⁠⁠

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Connect with Us:

Michael Momsen (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠)

Kai Lovel (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

Your mind plays tricks on you each day. We chat about leaning into the discomfort (often where your most valuable work will live), the Chair test, and getting *THE* shit done (not just the busy work).

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⚡️ This episode is brought to you by Earlywork Academy. Applications are open for their next tech sales cohort → ⁠⁠https://bit.ly/3KwIiBZ⁠⁠

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We referenced:

• Tim Urban's TED Talk (https://www.youtube.com/watch?v=arj7oStGLkU)
• Tolerating Distress PDF (https://www.cci.health.wa.gov.au/Resources/Looking-After-Yourself/Tolerating-Distress)

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Connect with Us:

Michael Momsen (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠⁠⁠⁠)

Kai Lovel (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

Following on from our war-time ep, we're chatting about how you can make reduce your chances of being laid-off by being a critical, valuable player in your startup (of any size).

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We referenced:

• AFR Article (https://www.afr.com/technology/the-question-scott-farquhar-asks-himself-to-weed-out-underperformers-20230718-p5dp8a)
• Netflix culture doc (https://jobs.netflix.com/culture)

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

You've seen the tech layoffs, heard about the broader economic climate, and perhaps the 'war-time' metaphor being used in startups right now. Why are we here, and how do you navigate it as a startup employee?

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Timestamps:

• (00:00) Intro
• (02:18) Radical efficiency
• (05:40) 1-in-60 rule
• (10:25) The evironment we're in
• (15:42) Investment in tech startups
• (22:02) Wartime v peacetime CEOs
• (26:53) Upside of wartime

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We referenced:

• AFR Article (https://www.afr.com/technology/tech-party-is-over-as-canva-and-atlassian-get-tough-and-perks-dry-up-20230706-p5dm5r)
• Book: Hard thing about Hard Things (https://www.amazon.com.au/Hard-Thing-About-Things-Building/dp/0062273205)
• Image: Starlink constraints (https://docs.google.com/presentation/d/1xE-a5P1dZkadstK4X5xfckecWfOZn2XqpdwAD9ebvO4/edit?usp=sharing)

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

So the deal has been won, the customer has signed. In a recurring revenue business, how do you keep them happy, healthy, and expanding? CSMs, PAMs, SAMs ... we explore the acronyms, team structures, and skillsets that all go into making a customer successful in a startup.

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

Michael and I are strong believers in taking as much risk as you can early on in your working life. Startups are an incredible place to do that, and that's what we're digging into today.

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

The ‘Product Engineer’ and how they build great products for customers

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

It's the US Military term which describes many startup environments well. We break down VUCA into it's parts, discuss how it shows up at Zipline, and share some tips for those operating in VUCA environment. This is a short and punchy one!

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⚡️ 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)

Kai Lovel (⁠⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠⁠)

📣 Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

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

Perhaps counterintuitively, mgmt consulting backgrounds can be a powerful asset in startups. We discuss why companies hire management consultants at all, the 7 Step Bulletproof Problem Solving Process, pyramid principle communication, and how you can sometimes overcook it.

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We mention:

• Podcast ep: McKinsey summarises Bulletproof problem solving — https://open.spotify.com/episode/7HUQSbNzoTf1gho5n8wc32
• Book: Crossing the Chasm — https://www.amazon.com.au/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986

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Connect with Us:

Michael Momsen (⁠⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠⁠)

Kai Lovel (⁠⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠⁠)

Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

We're not an everyone company. And you shouldn't join one either. Great companies are polarising. They can attract the right people with a strong magnet-like culture that pulls the right people in (with aligned values and ambitions) and repels the rest away. We discuss this in today's ep, and what Zipline's magnet looks like.

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Connect with Us:

Michael Momsen (⁠⁠⁠linkedin.com/in/michaelmomsen⁠⁠⁠)

Kai Lovel (⁠⁠⁠linkedin.com/in/kailovel⁠⁠⁠)

Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

There isn't a one-size-fits-all method for productivity. We discus several techniques such as using a daily highlights and "might do" lists. We also talk about the importance of finding the right balance between experimentation and execution and evaluating our success based on accomplishing important goals.

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We mention:

• Make Time by Jake Knapp: https://maketime.blog/book/

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Connect with Us:

Michael Momsen (⁠⁠linkedin.com/in/michaelmomsen⁠⁠)

Kai Lovel (⁠⁠linkedin.com/in/kailovel⁠⁠)

Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

Found yourself as the CEOs right-hand person? Or working in close proximity to a founder? We discuss the uniqueness of this working partnership, and how to make the most of it.

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Connect with Us:

Michael Momsen (⁠linkedin.com/in/michaelmomsen⁠)

Kai Lovel (⁠linkedin.com/in/kailovel⁠)

Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io

⁠

⁠Zipline.io⁠ is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at ⁠https://zipline.io

We discover a new latin word, and explore Ancient Greek philosophy, as we discuss the unspoken ‘second job’ every early startup employee has - to make their bosses life easier.

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We mention: • Podcast: Seeking Wisdom #19 - Carrying the Water - https://open.spotify.com/episode/08jrORqBuy9v2IAJ7w0q30 • Book: Ego is the Enemy by Ryan Holiday • Book: The Go Giver by Bob Burg

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Connect with Us:

Michael Momsen (⁠linkedin.com/in/michaelmomsen⁠)

Kai Lovel (⁠linkedin.com/in/kailovel⁠)

Feedback, ideas or career questions? Send us an email - ⁠kai@zipline.io⁠

⁠Zipline.io⁠ is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at ⁠https://zipline.io

In the world of startups, risk takes on a new depth. VC-backed unicorns, moonshot growth, and painful failure. How do you wrap your head around the risk of startups, and what’s the upside?

It’s a natural feeling when you’re pushing yourself into unchartered territory. Almost a certainty in the hurtlocker! But Imposter Syndrome can be crippling. We unpack where it comes from, why it exists, and how to wrangle it.

The age-old question, with an ever-changing answer. How do you uncover your strengths, play in your zone of genius, and spiral up your self-awareness? Mike shares 5 tips for honing in on your unique abilities, we talk about the Japanese concept of Ikigai, and explore what it means to back yourself.

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We discuss:

1. Follow the clues
2. Look for where there’s flow
3. Ask others
4. Ask surveys
5. Reflect in writing

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We mention:

• Link: Adam Grant on Tim Ferris Pod - Ep #399 (https://tim.blog/2019/12/05/adam-grant/)
• Link: PrinciplesYou (https://principlesyou.com/)
• Book: Find Your WHY by Simon Sinek (https://simonsinek.com/books/find-your-why/)
• Link: Self Authoring (https://www.selfauthoring.com)

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Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io

THIS is Michael's in-depth chat with Josh Neil from Next Chapter. Interviewing Michael for their founder newsletter, Josh digs into:

• 🔥 Warm intros, ❄️ Cold emails + tips for expanding network
• Developing a personal brand - is it worth it?
• Picking the startup (and industry) to join
• What's the best job strategy for future founders?
• and MUCH more

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Connect with Next Chapter:

Website - nextchapter.to

LinkedIn - linkedin.com/company/nextchapter-careers

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Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io

Michael shares a recent story of a micro-failure he experienced when presenting a segment at our all-hands. He explains his feelings, thinking, and process to get the 'gem' / learning from this failure, and grow.

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

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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 - maddie@zipline.io

Making travel moves with your current or new job - why this opportunity is unique to startups, how to weigh up your options when making a move, and how to immerse yourself in your new world.

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Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io

Humans are at the heart of businesses. Today we explore how organisations have different personas, how to treat your customers like humans, and how we can learn a lot from a family's Xbox purchase.

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Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io

WFH is a great tool for some. But if you're early in your career, what's the best mix of WFH v Office time? We speak about roles where WFH makes sense, some of our personal experiences being 'in the office', and ways you can make WFH work for you.

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Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io

We explore managing up, down, sideways — why it's actually work worth doing, and not just sucking up. Understanding your manager's job, sending great pre-reads, taking ownership of your goals, and much more.

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Jump to:
(00:00) Intro
(2:47) On stakeholder management
(6:37) Why is managing up so hard?
(8:19) Working with your boss
(13:51) What does your boss want?
(15:49) Pre-chewing your meat
(25:40) Tip 1: Weekly email 📌
(31:42) Tip 2: Pre-reads
(35:39) Tip 3: Understand your manager
(40:37) Traffic lights
(43:52) Maddie’s tips
(46:51) AJ’s tips
(48:31) Ivan’s tips

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Resources mentioned:
Link - Talk like a Consultant on YT (https://youtu.be/ppokRtCeuyI)

—

Connect with Us:
Michael Momsen (linkedin.com/in/michaelmomsen)
Kai Lovel (linkedin.com/in/kailovel)

Feedback, ideas or career questions? Send us an email - kai@zipline.io

Zipline.io is a fast-growing B2B SaaS startup solving frontline compliance challenges in healthcare. More at https://zipline.io