🤸♂️ Stop diving in headfirst
Podup | Best 3 Business Podcasts of the Week 🥉🥈🥇
GM, this is Podup #14. Discover the best 3 business podcasts of the week (save 2 hours 42 mins listening in the process).
What you need to know
🤸♂️ Stop diving in headfirst
💔 Learn to break your plans
💂♂️ How to headhunt lieutenants

Your positioning is likely wrong

Lenny's Podcast: Product | Growth | Career: April Dunford on product positioning, segmentation, ...
🥉 Third place (3 min read vs 1 hour listening)
Your positioning is never fixed. It should evolve as your idea turns into an MVP, as you build a scalable business model, and as you expand into new verticals. April Dunford is a master of positioning. She focuses on B2B SaaS, but her principles are helpful to all entrepreneurs and marketers.
What they say
April summarises positioning
I start with competitive alternatives. What do I have to beat in order to win a deal? [That includes the] status quo and competitors on the shortlist.
Once I’ve got that, I can make a list of differentiated capabilities. What capabilities do I have that the alternatives do not?
I can then translate those capabilities into value. This is the 'so what' for the customer. I’ll end up with 2 to 3 value buckets.
I can ask ‘What are the characteristics of a target account that makes them care a lot about that value?’ [This is my] target customer.
The last bit is market category. What’s the context that I position this thing in that makes my value obvious to the person I’m going after?
April Dunford
What should early stage companies do?
I get a lot of calls from companies that are super early stage. They’re not ready to over-tighten their positioning.
At that stage you have a positioning thesis. The best thing you can do is deliberately go through a positioning exercise and document the thesis.
The thesis says we think we can compete with these folks, we think this is differentiating, we think this is the value we can deliver that no one else can, these are the people we think will get excited by that, therefore this is the market we’re going to win.
Internally, it’s good for us to be in alignment. When I go to launch that externally, if I don’t have any customers yet, in my experience 100% of the time the thesis is partially incorrect.
It’s a bunch of assumptions based on what we did in customer discovery and the research we did before we built the thing.
April Dunford
What I say
Why it matters: Most people tend to start with messaging. They’ll dive head first into writing the landing page copy. When you’re launching a new product or service, avoid the urge to jump in blind. Take a second to scope out your surroundings with a positioning document.
It doesn’t take long - 30 mins tops if you know your business inside out. It gives you the right support to work on your messaging. It’s like bowling with the bumpers up as a kid - your chance of success is much, much higher.
Between the lines: Here’s an easy way to write your positioning statement:
For [your target market] who [target market need], [your brand name] provides [main benefit that differentiates your offering from competitors] because [reason why target market should believe your differentiation statement.]
Here’s what a real life example looks like for Podup:
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Sheryl Sandberg’s secrets to leadership

Masters of Scale: 5. Lead, lead again, w/Meta's Sheryl Sandberg on Apple Podcasts
Show Masters of Scale, Ep 5. Lead, lead again, w/Meta's Sheryl Sandberg - 7 Jun 2022
🥈 Second place (4 min read vs 40 mins listening)
I couldn’t care less about Sheryl’s wedding expenses scandal. As COO of Facebook, she helped Zuckerberg create one of the most powerful and ruthless companies in the world. That’s what I care about. The stories and frameworks behind her success and how I can apply this. So, without further ado, here’s a sneak peek behind the operational machine that is Sheryl Sandberg.
What they say
I believe to lead an organisation to scale, you need to be as skilled at breaking plans as you are at making them.
Everyday there are new competitors, new threats, and new opportunities.
There’s no simple, straightforward set of marching orders. It’s more like a dog fight.
Reid Hoffman
Every plan should be breakable
My team was 4 people. They were worried we were going to grow. So on my first day I said ‘Don’t worry, we’re all going to interview everyone.’
2 weeks later the team was 12 people. It was completely unreasonable for a person to have to interview with 12 people.
I had made a promise to make them feel good about scaling. I took it away in a week.
Sheryl Sandberg
Build for today with tomorrow in mind
I’ll give you another example, birthdays. We celebrated everyone’s birthday that day. Then it became that week.
Eventually, we had a huge sheet cake with quarterly birthdays. My team was 4,000 people when I left, and [the cake had] everyone’s name is on it.
Now it sounds like that didn’t matter, but it did. If you started out and celebrated everyone’s birthday and took that away, that’s a problem.
Now I’m not saying be mean and don’t celebrate birthdays. I’m saying figure out what your systems are going to look like later, and do it now.
Sheryl Sandberg
Your team should proactively flag problems
When our team was growing, I interviewed everyone who joined globally.
When we were at about 100 people, I noticed the queue to my interview was holding up the hiring process.
I said in a meeting with my direct reports that maybe I should stop interviewing, fully expecting they would jump right in and say ‘Absolutely not, you’re a great interviewer, we need your personal recommendation.’
Do you know what they did? They applauded.
I thought to myself ‘I’ve become a bottleneck and you didn’t tell me. That’s on me.’
Sheryl Sandberg
What I say
Why it matters: This episode is full of anecdotes like this. These are just but a few. Here’s my TL;DR takeaways:
1) Be adaptable to change your plans
2) Have strong views loosely held
3) Consider the impact of your decisions two years from now
4) Foster a safe space for colleagues to challenge the status quo
5) Take responsibility if 4) fails and do all you can to fix it
Between the lines: Medicspot is on its third pivot in as many years. As a healthcare startup, we’ve had to navigate the impacts of Covid, including an unprecedented change in patient behaviour. The biggest reason we not only stayed alive but thrived during Covid was because we excelled in these five areas.
No leader is right 100% of the time, particularly when a pandemic upends your entire business model. Our CEO, Dr Zubair Ahmed, was agile enough to pivot our plans as new opportunities started to emerge. Our team was (and still is) empowered to play devils advocate and challenge assumptions. This culture helped us make the right decisions and get outsized returns.

How to hire a leader

Lenny's Podcast: Product | Growth | Career: Gokul Rajaram on designing your product development ...
🥇 First place (4 min read vs 1 hour 2 mins listening)
I’ve found my new man crush. Before this episode, I’d never heard of Gokul Rajaram. Apparently, he’s a big deal. He’s on the board of Coinbase and Pinterest and is on the Executive team at DoorDash. In addition to a baller CV, he’s built an arsenal of deadly tactics over the years. Here are two of my favourites.
What they say
Gokul’s hiring playbook from Square
Companies ask me [for advice on how to hire] a leader for X, Y, Z function. I never respond with here’s this person.
If you want a playbook for hiring strong leaders in any function, look at companies who are best in class at that function in a similar space.
You’ve got to look beyond your competitors. You’ve got to look at folks serving [similar customers to you, like] SMBs, or enterprise, or consumers.
If you want to hire a Head of Marketing, you’ve got to find the top 3 to 4 companies that are excellent at marketing.
You don’t hire the person who is Head of Marketing at these companies. You hire the person who’s reporting to them, the lieutenant.
You have to build an org chart. It’s not hard, you just need to spend some time on LinkedIn. You go through the company and pick up the people.
I saw this in practice. Once Square went public, we were the only public FinTech in 2015. My goodness, our teams were raided. The next 2 years I saw huge chunks of teams in payments and compliance being raised by other FinTechs. Who was the best company in compliance? Square.
They didn’t go after our Head. They went after our lieutenant and the lieutenant of the lieutenant.
Gokul Rajaram
Don't give away titles cheaply
If you’re young, you have a unique opportunity as a founder to set a culture in place where people care more about scope and impact than they care about titles.
The titles I’m most opposed to are Director and VP titles. They lead to the most contention, conflict, disgruntlement and heartache.
Avoid granting VP and Director titles as long as possible.
The word Lead and Head of are both good because they describe what you do. The more words there are in a title, the more focused their role is.
Gokul Rajaram
What I say
Why it matters: These ideas are diametrically opposed. Why? The reason lieutenants are open to a move in the first place is to get a promotion and a change in title. But, this doesn’t mean you shouldn’t try to adopt both ideas.
Poach the best lieutenants and give them the promotion they’ve been striving for. Just make sure you avoid VP and Director titles for as long as possible and put a greater emphasis on your mission, culture and the impact they can have at your company.
Between the lines: I’m not sure if I made it clear at the start, but I love both of these ideas. The first is something I was doing already, just on a smaller scale.
When I needed a Marketing Manager for a woman’s health brand at Medicspot, I approached Marketing Executives - the lieutenants of the lieutenant - from D2C fashion and beauty companies that are strongest in marketing. It worked for me and is an approach I’d recommend to any hiring manager, regardless of your department or seniority.

Note, these quotes were pulled at different points of the episode. Some sentences were left out to make the narrative clearer and more concise. Podup is not associated or affiliated with any podcast (unless otherwise stated). All roundups are independently written and do not imply any sponsorship or endorsement by the podcast.