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12 months ago I decided that I would be taking over the marketing team as the acting CMO
This decision was strange to many. Because I don’t have professional training as a marketer.
My entire career has been created around building products with massive engagement and reach.
I got a lot of people trying to discourage me from it
It’s not the first time I heard reasons to NOT start something. Because of the risks associated with it. I heard it before when I left to New York from a completely different world and when I started Chili Piper (my first company too)
But every single time I started something completely new and unfamiliar I had a strong rationale for doing it
In this particular case, wanted to be a Revenue Operator at scale myself. The operator experience would allow me to be a better BUILDER for Revenue teams . Plus a lot more reasons , you can see them detailed here
The decision both excited and terrified me
Terrified me because I knew I didn’t have direct experience as an operator and I was afraid I would make too many mistakes and our pipeline would suffer.
I was right to be afraid - I did make mistakes.
Four of the biggest mistakes I made at the beginning:
1. Underestimated the power of collaboration in marketing and underplayed it. I wish I could go back in time and nurture it more
2. The second mistake I made was to think that a very important skill in marketing is the ability to use fancy words to get your audience to take action.
ChatGPT showed me it’s easy to throw persuasive words on a page. What’s hard is to do thinking/research/mentalization behind those words
To fully understand the words that resonate with YOUR audience
Overnight everyone got an upgrade on writing and showed me I was dead wrong to put so much emphasis on developing my “fancy” vocabulary
[no chatGPT prompt was used in writing this article - I prefer to leave myself unedited to keep my humanity intact but also because i believe the process of writing helps me become a better thinker too]
(also no content person helped me with editing — this is 100% me)
3. I was so afraid I was underqualified for the role I became very sensitive to feedback. Because I was my worst critic I antagonized over everything
4. I was low on spirit coming from a big layoff and I didn’t know how to get myself back on track fast enough. It’s hard to stir a ship with a broken spirit. Mindset is key and took a while to get to my normal self
Luckily I was surrounded by a supportive team that had patience with my ups and downs and helped me learn to get better and course correct. Don’t know what we would have done without one another
This team helped me a lot through this journey and I am forever grateful
These past 12 months we had many highs and many lows
Some months we had record conversion rates in our funnel. Record months for pipeline created from certain channels. Record months for closed won
But we also had months where we didn’t meet our quota. Those months left deep scars
These scars helped me realize that being directly responsible for such a big chunk of the business success is very HARD
But these scars I wouldn’t reverse. And I don’t regret making the switch to marketing one bit
Because of them, I learned a lot. And I’m a lot more equipped to be able to hire my replacement
I will write my learnings below. I had many of them - some might sound obvious to experienced marketers
But I did want to leave a trace of them as a testament to how much growth happens when you put yourself in uncomfortable places
I was right to be excited about this decision too
Because it turns out I learned a whole lot more than I imagined I would
There are three big learnings that have transformed me a great deal
1. Deeper understanding of the power of the ecosystem
Even though we focused on building communities ever since we started Chili Piper I hadn’t truly solidified this muscle until this year. The power of the ecosystem compounds everything. And when you combine multiple channels that’s when magic happens
2. By far my biggest learning in the past 12 months was an upgrade in my communication skills.
I went from the geek who only understood code and UX and never wrote any docs (except for product specs and some presentations) to the person who writes lots of articles and just finished a book about my biography as well
I am by all means still a work in progress. But by learning to use words in better ways I can become a more effective co-CEO going forward
3. You can’t direct/lead anything of great impact unless you have a deep understanding of people
I always liked to observe people - my users - to build great products for them.
But this marketing journey has taught me that no matter how great your product is, it doesn’t matter if you don’t know how to move people at scale to take action in the first place
You need product market fit but you also need language market fit that resonates
And you can only pass the chasm to reach the top SaaS companies that go IPO if you have the ability to understand deeply WHY people do what they do at scale
Here are my other 39 (!) learnings in no particular order
Fast wins over perfect. Always
Partnership with a strong data team makes or breaks marketing. You can’t make decisions on gut alone
With all the progress in AI and data analytics, marketing is as much about understanding data as it is about understanding human behavior. The ability to draw insights from data while staying empathetic to human emotions and needs defines successful campaigns
Empathy has ROI: One can only understand people with a lot of empathy. In a world where we’re all bombarded with information , the brands that genuinely understand their customers stand out
People are more likely to connect with stories than with facts and figures. Storytelling as a skillset is hard to learn
Creating good content is HARD. You have to educate, entertain, and inspire. In a sea of AI-generated content is getting even HARDER
Marketing is a team sport more than any other department. Because:
Buy-in from others is key. The ability to get buy-in from your own team and other internal teams is both an art and a science. Yet one can’t succeed without it when driving new campaigns
Infectious belief. If you are not convinced of your campaign success no one else will be. Your mindset is the driver of your success
Mindset is everything. Standing out in a pool of competitors takes guts to do things differently. It’s hard to have the courage to stand out in a downturn
EX (aka Employee Experience) is as important as CX (aka Customer Experience) . Marketing touches a lot of things in the customer life cycle. However, a lot of brand is impacted by the employee experience
Internal culture is a lot more important to the brand than anything else. Internal culture is hard to steer. Especially in a downturn
Maniacal about adding value to people (your employees, your partners, your customers, your prospects) always wins
Customer success is the most powerful marketing tactic. Customer success is everybody’s job in the company
Hands-on learning is the best way to accelerate knowldge. No book or article or course can teach you marketing as well as a failing landing page you created
Consistently showing up with hands-on learning to get better beats natural talent any time
Top skill in marketing is understanding the human mind. How people make decisions and why. I mapped all the skills that i found important in every marketing role
Pivoting fast is a critical skill. There are a million ways to succeed in marketing. But there are also a million ways to fail.
It’s easy to get lost in priorities (events, content, pages, social) but the # 1 priority is talking and listening to customers
Any conversation with a prospect, a customer, or a partner is a learning opportunity. Have many of them
Keep an eye on results at all times. Marketing in 2023 is a lot different than marketing in 2018 because of the sea of bots and tools and it keeps changing. You have to be open to change at all times. Yet constantly seek results
Aligned GTM at scale happens when metrics align between the teams. Attribution is highly controversial in most teams except those that understand creating pipeline is a team sport, not a contest
Big changes can’t happen unless there’s GTM alignment with sales, customer success and product
Consistency/repetition are a powerful skill in marketing
To be top of mind for those that are not yet ready to buy , you have to repeat repeat repeat the same message 1000 times even if you are bored of it
Marketing requires you to fire from all cylinders at all times. Be creative, social, analytical, hands-on, and strategic. It’s both exhilarating and exhausting all in one. Especially in the era of AI
You have to be really good at partnering with your peers. Like really really good. You don’t survive in a blame game. Aligned GTM teams always win in the long run
Brand impact is oftentimes misunderstood because most people don’t measure it . We measure some of it and that helps a lot
Brand work is critical: standing out is more important than perfect. Attention is the most scarce resource - you can’t stay top of mind if you are not standing out
Never automate something before you understand how to make it work manually really really well . Understand all the ins and outs before you put the tools in place to automate
Really really good targeting is really hard and yet makes the biggest difference in converting audiences. Takes a million tools to stitch to get it right
Invest in your personal brand. Without it, you are not top of mind when you are not in the room
It is not as glamorous as it looks. The things that might look glamorous from the outside in marketing are typically the kind of things that require the most boring work behind the scenes
Tough skin is essential. If I wasn’t in marketing I would probably delete my LinkedIn, my Instagram, and my TikTok. Social media can be brutal at times
Best ideas come while I’m walking not at my desk
The first time you will do something, it will most likely suck. Magic happens when you have the patience to continue at tinkering with it until you perfect it
Surround yourself with people who are gentle on your mistakes. No books or or work have contributed as much to my acceleration of knowledge as my mistakes did
Underrated skill: taking complicated things and making them look simple
Be understood. Goal of marketing messaging is to be understood, not to sound fancy or smart
Street talk always wins in A/B tests over fluffy words
Marketing is a misunderstood term. Everything that touches the customer /prospect is marketing (nearbound, allbound, plg, partnerships, it gets overwhelming fast)
Most titles in marketing are confusing. No two demand gen functions are alike
Fun is an underrated part of marketing. If you are not having fun it’s hard to stay motivated. Find the activities that bring back the fun into work and drive results as well
Constantly reinventing yourself is key to success . There are many ways to do marketing well. Once you figure it out your competitor does as well.
Great ideas for something new won’t work at first. Requires lots of patience to water a new idea to full potential
The more you know about marketing the more you understand how little you know about marketing. Human minds are complicated, and the ecosystem in which we live is even more so. Learning about the human mind is a beautiful, never-ending journey
12 months ago I decided that I would be taking over the marketing team as the acting CMO
This decision was strange to many. Because I don’t have professional training as a marketer.
My entire career has been created around building products with massive engagement and reach.
I got a lot of people trying to discourage me from it
It’s not the first time I heard reasons to NOT start something. Because of the risks associated with it. I heard it before when I left to New York from a completely different world and when I started Chili Piper (my first company too)
But every single time I started something completely new and unfamiliar I had a strong rationale for doing it
In this particular case, wanted to be a Revenue Operator at scale myself. The operator experience would allow me to be a better BUILDER for Revenue teams . Plus a lot more reasons , you can see them detailed here
The decision both excited and terrified me
Terrified me because I knew I didn’t have direct experience as an operator and I was afraid I would make too many mistakes and our pipeline would suffer.
I was right to be afraid - I did make mistakes.
Four of the biggest mistakes I made at the beginning:
1. Underestimated the power of collaboration in marketing and underplayed it. I wish I could go back in time and nurture it more
2. The second mistake I made was to think that a very important skill in marketing is the ability to use fancy words to get your audience to take action.
ChatGPT showed me it’s easy to throw persuasive words on a page. What’s hard is to do thinking/research/mentalization behind those words
To fully understand the words that resonate with YOUR audience
Overnight everyone got an upgrade on writing and showed me I was dead wrong to put so much emphasis on developing my “fancy” vocabulary
[no chatGPT prompt was used in writing this article - I prefer to leave myself unedited to keep my humanity intact but also because i believe the process of writing helps me become a better thinker too]
(also no content person helped me with editing — this is 100% me)
3. I was so afraid I was underqualified for the role I became very sensitive to feedback. Because I was my worst critic I antagonized over everything
4. I was low on spirit coming from a big layoff and I didn’t know how to get myself back on track fast enough. It’s hard to stir a ship with a broken spirit. Mindset is key and took a while to get to my normal self
Luckily I was surrounded by a supportive team that had patience with my ups and downs and helped me learn to get better and course correct. Don’t know what we would have done without one another
This team helped me a lot through this journey and I am forever grateful
These past 12 months we had many highs and many lows
Some months we had record conversion rates in our funnel. Record months for pipeline created from certain channels. Record months for closed won
But we also had months where we didn’t meet our quota. Those months left deep scars
These scars helped me realize that being directly responsible for such a big chunk of the business success is very HARD
But these scars I wouldn’t reverse. And I don’t regret making the switch to marketing one bit
Because of them, I learned a lot. And I’m a lot more equipped to be able to hire my replacement
I will write my learnings below. I had many of them - some might sound obvious to experienced marketers
But I did want to leave a trace of them as a testament to how much growth happens when you put yourself in uncomfortable places
I was right to be excited about this decision too
Because it turns out I learned a whole lot more than I imagined I would
There are three big learnings that have transformed me a great deal
1. Deeper understanding of the power of the ecosystem
Even though we focused on building communities ever since we started Chili Piper I hadn’t truly solidified this muscle until this year. The power of the ecosystem compounds everything. And when you combine multiple channels that’s when magic happens
2. By far my biggest learning in the past 12 months was an upgrade in my communication skills.
I went from the geek who only understood code and UX and never wrote any docs (except for product specs and some presentations) to the person who writes lots of articles and just finished a book about my biography as well
I am by all means still a work in progress. But by learning to use words in better ways I can become a more effective co-CEO going forward
3. You can’t direct/lead anything of great impact unless you have a deep understanding of people
I always liked to observe people - my users - to build great products for them.
But this marketing journey has taught me that no matter how great your product is, it doesn’t matter if you don’t know how to move people at scale to take action in the first place
You need product market fit but you also need language market fit that resonates
And you can only pass the chasm to reach the top SaaS companies that go IPO if you have the ability to understand deeply WHY people do what they do at scale
Here are my other 39 (!) learnings in no particular order
Fast wins over perfect. Always
Partnership with a strong data team makes or breaks marketing. You can’t make decisions on gut alone
With all the progress in AI and data analytics, marketing is as much about understanding data as it is about understanding human behavior. The ability to draw insights from data while staying empathetic to human emotions and needs defines successful campaigns
Empathy has ROI: One can only understand people with a lot of empathy. In a world where we’re all bombarded with information , the brands that genuinely understand their customers stand out
People are more likely to connect with stories than with facts and figures. Storytelling as a skillset is hard to learn
Creating good content is HARD. You have to educate, entertain, and inspire. In a sea of AI-generated content is getting even HARDER
Marketing is a team sport more than any other department. Because:
Buy-in from others is key. The ability to get buy-in from your own team and other internal teams is both an art and a science. Yet one can’t succeed without it when driving new campaigns
Infectious belief. If you are not convinced of your campaign success no one else will be. Your mindset is the driver of your success
Mindset is everything. Standing out in a pool of competitors takes guts to do things differently. It’s hard to have the courage to stand out in a downturn
EX (aka Employee Experience) is as important as CX (aka Customer Experience) . Marketing touches a lot of things in the customer life cycle. However, a lot of brand is impacted by the employee experience
Internal culture is a lot more important to the brand than anything else. Internal culture is hard to steer. Especially in a downturn
Maniacal about adding value to people (your employees, your partners, your customers, your prospects) always wins
Customer success is the most powerful marketing tactic. Customer success is everybody’s job in the company
Hands-on learning is the best way to accelerate knowldge. No book or article or course can teach you marketing as well as a failing landing page you created
Consistently showing up with hands-on learning to get better beats natural talent any time
Top skill in marketing is understanding the human mind. How people make decisions and why. I mapped all the skills that i found important in every marketing role
Pivoting fast is a critical skill. There are a million ways to succeed in marketing. But there are also a million ways to fail.
It’s easy to get lost in priorities (events, content, pages, social) but the # 1 priority is talking and listening to customers
Any conversation with a prospect, a customer, or a partner is a learning opportunity. Have many of them
Keep an eye on results at all times. Marketing in 2023 is a lot different than marketing in 2018 because of the sea of bots and tools and it keeps changing. You have to be open to change at all times. Yet constantly seek results
Aligned GTM at scale happens when metrics align between the teams. Attribution is highly controversial in most teams except those that understand creating pipeline is a team sport, not a contest
Big changes can’t happen unless there’s GTM alignment with sales, customer success and product
Consistency/repetition are a powerful skill in marketing
To be top of mind for those that are not yet ready to buy , you have to repeat repeat repeat the same message 1000 times even if you are bored of it
Marketing requires you to fire from all cylinders at all times. Be creative, social, analytical, hands-on, and strategic. It’s both exhilarating and exhausting all in one. Especially in the era of AI
You have to be really good at partnering with your peers. Like really really good. You don’t survive in a blame game. Aligned GTM teams always win in the long run
Brand impact is oftentimes misunderstood because most people don’t measure it . We measure some of it and that helps a lot
Brand work is critical: standing out is more important than perfect. Attention is the most scarce resource - you can’t stay top of mind if you are not standing out
Never automate something before you understand how to make it work manually really really well . Understand all the ins and outs before you put the tools in place to automate
Really really good targeting is really hard and yet makes the biggest difference in converting audiences. Takes a million tools to stitch to get it right
Invest in your personal brand. Without it, you are not top of mind when you are not in the room
It is not as glamorous as it looks. The things that might look glamorous from the outside in marketing are typically the kind of things that require the most boring work behind the scenes
Tough skin is essential. If I wasn’t in marketing I would probably delete my LinkedIn, my Instagram, and my TikTok. Social media can be brutal at times
Best ideas come while I’m walking not at my desk
The first time you will do something, it will most likely suck. Magic happens when you have the patience to continue at tinkering with it until you perfect it
Surround yourself with people who are gentle on your mistakes. No books or or work have contributed as much to my acceleration of knowledge as my mistakes did
Underrated skill: taking complicated things and making them look simple
Be understood. Goal of marketing messaging is to be understood, not to sound fancy or smart
Street talk always wins in A/B tests over fluffy words
Marketing is a misunderstood term. Everything that touches the customer /prospect is marketing (nearbound, allbound, plg, partnerships, it gets overwhelming fast)
Most titles in marketing are confusing. No two demand gen functions are alike
Fun is an underrated part of marketing. If you are not having fun it’s hard to stay motivated. Find the activities that bring back the fun into work and drive results as well
Constantly reinventing yourself is key to success . There are many ways to do marketing well. Once you figure it out your competitor does as well.
Great ideas for something new won’t work at first. Requires lots of patience to water a new idea to full potential
The more you know about marketing the more you understand how little you know about marketing. Human minds are complicated, and the ecosystem in which we live is even more so. Learning about the human mind is a beautiful, never-ending journey
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