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In this mail:

1. The Role of a Founding Designer: with Ivy Mukherjee

2. Insight into what’s happening in design leadership

Ready? Get a coffee, Matcha, Green Tea and enjoy. ☕️

“Tom, my co-founders and I are struggling to hire a designer for our early-stage start-up”

This is one of the most common messages I receive on a weekly basis. Founders often don’t know where to look, what they need, or the nuances of design, which is understandable.

I believe in 2023, more designers are looking for meaningful challenges, there is no job security anymore as we’ve seen with layoffs, so working for a start-up is enticing.

I sat down with Ivy Mukherjee, a world-class designer focused on growth, 0-1 and has worked with some of the greatest design teams as well as now in the start-up world on her thoughts about the role of a founding designer, how to hire the best designers for your roles and the realities of being a solo designer.

Ready? Let’s go. Get a coffee, breathe and enjoy. ☕️

The Ultimate Guide to the Founding Designer Role

1 - What are the challenges of being a founding designer?

Startups are designed to be hard and literally no day will feel the same. The highs are very high and lows can even break you at times. With that said, they are also very rewarding and that’s one of the primary reasons people start or join a startup.

There can be multiple different challenges in a startup and this is my ongoing list, which goes beyond the hard skills of a designer:

• Keep your mental and physical health in check: first things first - in order to do good work, collaborate well, explore fast and iterate enough you need to make sure your body is in sync with yourself. Get enough sleep, meditate, run, strength train or anything that works. But make sure you are taking care of yourself. Startups can be intimidating, so be selfish and take time out for yourself in order to make sure your tomorrow looks better. Do this for yourself.

• Too many challenges to be solved at the same time: There is always something on fire and needs your attention, but ruthless prioritization is the name of the game. Remember, every decision will have its consequences. Are you comfortable with X over Y? If so, how comfortable are you? What are the business stakes? What happens if you can’t prioritize Y for the next few weeks? People will look up to you and your hypothesis, insights as well. So, being comfortable with which project to take over others is very important.

• Forget your picture perfect double diamond process: I can’t stress on this enough. I might get into trouble here with fellow designers here, but let me say - there is no picture perfect process to designing good products and no one framework works for all or in every company or in every situation. Be adaptable, be bold in your approach and be more than okay to change your process with the need of the hour. But that also doesn’t mean you have to bend over backwards to fulfil every task from everyone.

• You will do a lot more than what your job entails/lines are blurred in between different roles: There will be a lot of problems which are not well defined or nobody is there to define it for you. A big part of you growing as a founding designer is to define problems, why the problem is a problem and what are the different ways of solving it without having a full fledged team. And trust me it can be a lot of fun. An opportunity is as big or as small as you want it to be. Ask yourself if you are okay with it.

• With great power comes great responsibility: Everyone wants more power and control, but very few can deal with the responsibility that comes with it. Ask yourself if you are okay with being questioned on your decisions, if you are okay with being uncomfortable for days and being okay with personal hockey stick growth. Imagine yourself in those situations and see how okay you are with it.

• You don’t have the luxury of time: You don’t have all the days and weeks to work on optimising. There will be, but it might not be now. My manager keeps saying this fascinating sentence: “ always think of how much we can do in a week’s time and let’s push through that” and it has stuck with me. I found it really valuable in how to think of time, prioritizations and what can be done.

• Thinking slow, fast and beyond: Now this is a tough nut to crack and you will only get better with time and experience. Solving for MVP, yet solving for the future so the system doesn’t break. Always imagine what your north star vision is and work backwards with different shipping cycles. You will also realize how far you and the product have come.

• Imposter syndrome: I work with a bunch of magnificent colleagues who are incredible at what they do and beyond so. You are bound to feel like an imposter. But growth happens when you surround yourself with people who are extremely talented and passionate about what they do.

2 - What is the driving factor for you to join early-stage startups?

Let me start by saying, don’t join a startup for a flashy designation like “founding designer” or “head of design”. There is a good chance of you being disappointed if that’s the sole driving factor.

I wanted to solve for -

• Evergreen problem space(s): Startups working on problems which are heavily rooted into our day to day life and ecosystem. Also, they are generally hard to uproot with some external changes.

• Problems which I am inherently passionate about: This boils down to being self aware - which kind of problems excites you the most, where you can see yourself thriving, where you are even 1% better than other folks, where your 1st principle thinking kicks in. You ideally don’t want to challenge yourself in every aspect while joining a start-up.

• Nimble team with incredible people: 10yrs in the industry and I have realized people can make or break your experience in a company. So, I personally take bets on people. You will be working with them 8hrs a day, 5 days a week in the years to come. You better enjoy working with them and vice versa. I also wanted to move fast and iterate at a much faster pace, hence the decision to move to early-stage.

• My growth as a designer and beyond that: I recently turned 30 and the idea of starting something of my own is becoming more real to me. I wanted to somewhat simulate what it is like to be in a start-up and grow with the product(s), people and company. I wanted to grow as a designer and beyond that - this is more of a self discovery journey too.

3 - How can companies set up founding designers to succeed?

• Don’t expect designers to come in and tell you the importance of design on a daily basis: Designers can relate hard with this one! One of my foremost criteria to join any company was to make sure the leadership values design and understand the importance of it and I am so delighted to see it in my current company (touchwood). You don’t hire engineers or sales folks and keep on asking them what is the value of a good engineering system or good sales pipeline right? Please stop asking designers on a daily basis, how this will move the needle. Good design brings trust and trust brings and retains customers. If you have doubts about it, please do the research yourself.

  Also designers, please find out leadership/companies who value design. You will be tired of having an upward battle every day.

• Culture/values of the company: This is a 2-way street - what do you value and believe in. And see if the culture is mostly matching to yours. Also, how the company historically has stood up with their values and culture. Ask questions with examples.

• Define which kind of designer you are looking for: Different companies in different spaces will have various needs. Ideally, you want a unicorn, but they aren’t real, right? 😄 So, defining which kind of designer you will need at least for the next 1-2 years will be very helpful for you and also for the prospective candidates.

• What does success look like: You need to understand what the expectations are from you. What does mutual success look like in the 1st month, first 3 months, 6 months, 1 year and beyond this will be an evolving process? So, keep having these conversations on a daily basis.

• Decision documentation: Written documentation culture is a no-brainer. As a company, you are taking hundreds and thousands of decisions on a daily/weekly basis. So, making sure it's documented somewhere is very important to gather all the historical context. Even for designers this is true once you join any company - make sure you document your decisions with reasoning and also communicate them in your team(s).

4 - What should the first 100 days look like for a founding designer?

• getting to know the product inside out: The best way to start working on a product is to use it daily and also document the good things and not-so-great things. This can be a great primer for your chats with different people and questions to them.

• build relationships with your inner team and outer team: Do a lot of calls with your immediate team and get to know the outer team who also influences decisions and what should be built. This has compounding effects in the long run - truly understand their problems and see if and when you can solve some of them.

• reading through decisions: Read through the history of the company, their customers, what they have been up to and why. Do your own mind-mapping exercises to make sense of how things are and ask a bunch of questions. Remember, you are very new, so you have the card to ask any and every question.

• read about the business model: Understand what they are trying to solve, how they make money and what the future looks like. As you grow in your career this becomes more and more important. Challenge yourself to understand the business model and if you can’t understand certain parts - ask questions.

• understand what the company and leadership values are: A big part of you being a good designer is to understand what the leadership values are and how you can deliver them. This is a combination of 1:1s, all hands, self-awareness and how they react to different situations. This is not a one-time problem-solving - it's a lifelong process.

• Attend sales/customer calls: Always be listening and taking notes. Be as close to the customers as you can be. Make the GTM team your best friend. You want to show your work to customers, get feedback, make iterations and keep listening to how they are using your product, what they are working towards and how you can positively surprise them. This will solidify your decisions and help you make better and more relevant products.

• building a working design system: You want to make your life and the fabulous engineering teams’ work as easy as possible. Please make sure to build a robust design system which works for 70% -80% of the product lines but also remember to not waste your time building deliberate and rigid design systems as the system is supposed to evolve and grow.

5 - Where can designers find founding design roles?

• Follow prominent Venture Capital fund’s portfolio companies’ talent portals and get accustomed to their recruiters. I have met some fantastic recruiters over the years and got connected to great founders as well.

• Specific recruitment agencies working exclusively for founding designers or early-stage roles

• Twitter, Otta.com, read.cv can be really helpful too

6 - What kind of designer do you need to be to join as a founding designer?

TL;DR - my personal suggestion will be to work for at least a few years in order to be a “good” founding designer at a fast-growing early-stage company, or else it can be very overwhelming at times.

• Self-aware to take the hit: highs can be really high and lows can be really low. So be mentally prepared for it.

• Be a Ferrari, but don’t forget to refuel: You don’t need to speed up to full throttle every day, but knowing when to be a Ferrari and when to refuel yourself is going to be crucial. You have to set clear expectations and be true to yourself.

• Be ridiculously good with your craft: Your strategy and research will be meaningless if you are not good at your craft. At the end of the day, you will be judged based on the output you create. Be confident about your craft. No sugar coating here. You are a designer after all and craft is a big part of it.

• Be entrepreneurial: Best founding designers will know when and how much to cut corners. What can be achieved in a minimal team or time set-up. Or even when to go all out as well when that is going to be the most pivotal point of the company.

• Have a good grasp of how products and people work: Understanding products, markets and people in both macro and micro levels will be super beneficial. For example - which products in which markets might work and how people in those markets behave as well.

Insights into the Design Leadership Job Market

I’ve said before companies are in survival mode. They care about the next 3 months, not how design can infuse business strategies for years to come. They know they need design, but some are struggling to get the best talent due to budgets etc.

A quick snapshot of what I am seeing, mainly in large orgs:

- New CEO comes in.
- Design gets diluted at the top.
- Move from a centralised function to decentralised.
- Lose the design leader or they leave.
- Design sits in product teams.
- Designers want to leave, poor retention etc.

C-Suite changes are affecting design more than ever. Mainly, because they don’t see how design can infuse the business strategy 3-10 years out and need to cut costs now.

Often, a high-end consultancy will come in at CEO/Board level for strategic input and 3 months later they have their designers in the team. This is happening a lot.

I predict for the next 12-18 months consultancies will be used more, and cut costs until in-house leadership has a resurgence again.

That’s a wrap, thank you for reading.

Quick note:

• If you’re looking for a new design role please consider signing up for our invite-only talent network. This is where we talk to designers about live roles, as well as more community features coming soon - https://itsverified.typeform.com/apply

• If you’re looking to make hires, want insights into the market, figure out what the best designers and leaders are looking for, we’ve come out of the “beta” phase now, and are ready to go all in, so please do get in touch.

You can also reply to this email if you have any questions, thoughts, concerns, or challenges with finding a new role or figuring out your next career move. Me and the team are here to help.

Over the next 7 days I will be bringing 2 interviews:

• The Human Cost of Broken Design with Thomas Wilson

• Unlocking Career Potential: The Importance of Business Knowledge for Designers with Alen Faljic.

Until then! ❤️

Tom