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.

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!

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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

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

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 - maddie@zipline.io

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 - maddie@zipline.io

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 - maddie@zipline.io

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 - 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

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.

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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

—

⚡️ 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.

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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

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.

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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

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