Advice & resources

Sufficiently down-to-earth founders will, by default, convince themselves that they won’t succeed. This is partly because down-to-earth people are rarely successful in anything grand. It’s partly because everything looks simultaneously harder and easier before you try it. And it’s partly because all good ideas sound like bad ideas until they come to fruition.

Every startup needs a repeatable and sustainable sales model. This week, we explore the various strategies that work for SaaS products.

Tough economic conditions have a way of forcing us to do what we should have always been doing. This year, startup leaders need to make sure their teams are focused on the right things.

Today, we cover the two most tempting (and fraught) pivots for B2B startup founders: moving down-market, and adding additional product lines. We explore why these shifts are so difficult to pull off, and how to get them right.

A self-service experience, including a free trial or freemium plan, is a cost-effective way to sell a product that is capable of selling itself. Many startup leaders underestimate how much work it takes to truly make this work, though. This week, we explore how to deliver a self-service SaaS experience, and how to decide whether this strategy for growth is right for you.

For many SaaS companies and startup leaders, the 2022-2023 recession will be their first. This week, we look at how SaaS companies can optimise costs, adjust their value proposition, and build a strong business during a recession.

As startups achieve product-market fit, product strategy simultaneously becomes more important and more difficult. Startups become unfocused by chasing new opportunities when they should be optimising what they’ve already brought to market. This week, explore the importance of focus as you scale your SaaS company.

As your startup grows, responsibilities that used to belong to a single individual will be owned by teams and, eventually departments. This transition is where startup operations become critical. This week, we explore some of the rituals teams should adopt for continuous improvement.

Despite all startups being resource-poor relative to what they are trying to achieve, many founders invest in solutions (e.g., specific product features, technology improvements, and internal systems/processes) that require effort beyond what is desirable from an ROI perspective.

Sufficiently down-to-earth founders will, by default, convince themselves that they won’t succeed. This is partly because down-to-earth people are rarely successful in anything grand. It’s partly because everything looks simultaneously harder and easier before you try it. And it’s partly because all good ideas sound like bad ideas until they come to fruition.

Many founders burn out because they’re always praying for the problems to finally ease. And, sure, you will occasionally experience short periods where things seem to be going well. But it’s always only a matter of time before your success leads to more challenges.

It can be difficult to convince a customer to adopt your product when they already have a solution they’re happy with. This is why disruptive products typically need to be radically better, radically cheaper, or both. However, thanks to platform envelopment, it’s actually possible for a notably worse app to disrupt superior incumbents.

Most managers in early-stage startups think that chaos is inversely correlated with results. That is, they think that chaos breeds bad results and an unhealthy environment, while order breeds good results and a more harmonious environment. This perception is wrong.

To win, startups need to lean into their advantages because they’re a decade away from the kinds of moats enjoyed by established corporations. This means they need to work smart (i.e., mostly do the right things) and work hard (i.e., execute at a pace and with intense risk tolerance).

Many startup leaders shy away from the most painful problems. Whether it’s too hard to build, too hard to sell, or requires massive scale to achieve viable economics, there are many reasons to put opportunities in the too-hard basket. But tackling difficult problems is how we build differentiation in startups.

Startups are ideas in action. However, not all ideas are created equal. Let’s explore how startup leaders can use the concepts of feasibility, desirability, and viability to quickly and reliably validate startup, product, and feature ideas.

The best strategies and ways of working for early-stage companies can lead to chaos and quality problems for mature companies. Similarly, early-stage companies that adopt mature ways of working can move too slowly and burn through runway, when they should be finding product-market fit.

As you build a startup, selecting the right problems to solve and coming up with effective solutions is crucial. The principles of divergence and convergence can help leaders to understand and improve the problem-solving process.

The best startups are committed to outcomes. In an idea meritocracy, all people raise ideas, regardless of their position. Ideas are rigorously evaluated, quantified, and debated.

First-mover advantage argues that businesses first to enter a market have an advantage over latecomers. This common-sense idea discourages prospective founders, giving them the impression that they are too late to tackle a problem they’ve identified because someone else got there first. While first-mover advantage exists and has helped some projects establish a lead, there are many counter-examples where very late market entrants have won. In fact, the benefit of being late into a market often outweighs the costs.

Differentiation is required to build a great startup. This means you need to do things differently. But you can’t reinvent everything as you go: founders need to recognise where it makes sense to be contrarian, and where it makes sense to adopt common practices. This week, we explore the value of contrarian approaches in startup building, and the way the introduction of AI copilots impact this principle

Teams can tackle increasingly ambitious initiatives if they learn to challenge risky assumptions with proofs-of-concept, research, and other forms of experimentation.

For something that startups pay little attention to, pricing greatly impacts business outcomes like growth, revenue, profitability, and viability. But, some second-order consequences are just as important. This week, we explore how great pricing models can make it easy to prioritise initiatives within your startup.

Startup leaders want to integrate AI into their products. Prospective founders want to build businesses on top of AI. Investors wish to create alpha. Today, we explore how startups can capture value when deploying AI.

This week, we explore the difference between vertical and horizontal SaaS products and how verticalisation can be the best way to win in the increasingly competitive software-as-a-service market.

When you build a startup, it can feel like you’re constantly solving new operational problems within your teams. This week, we explore how by solving each problem in the right place in your business, you can build a simpler and more operationally effective business.

Partnerships can drive growth and augment your product at all startup stages, but getting started is difficult. This week, we explore how partnerships typically work for B2B SaaS startups and how to start utilising them.

This week we explore a versatile research exercise that can help you to pivot or improve your product based on the needs of your users.

Most startups are idea-rich and resource-poor. Founders and product managers are constantly bombarded with feature requests, so a lack of ideas is rarely the biggest problem. At the same time, startups typically try to achieve something ambitious with limited resources. Startup success is thus heavily dependent on what you say yes and no to and how you prioritise these initiatives against each other. I encourage teams to focus on complex problems faced by many rather than those faced by few. This is the best way to differentiate your product and find product-market fit.

Startup success is all about momentum. This is because startups do not have a great starting position to fall back on — they typically start with no customers, a small team, and no viable product. This means that you’re catching up for as long as you’re a startup. You’re catching up to the incumbents you’re trying to disrupt, to the competition which got a head start, to unrelated businesses with whom you’re competing for investment capital.

For many enterprise SaaS products, a layer of professional services is essential because enterprise customers tend to have diverse needs from each other. Professional services enable deeper customisation on a per-customer basis while keeping the core product focused on the target market rather than the needs of specific customers. Another benefit of providing in-house professional services is that they can provide a significant revenue stream during the early days of finding product-market fit. Many bootstrapped companies use this revenue to keep the lights on as they build recurring revenue momentum.

Most companies stumble across a market with a problem and spend most of their early-stage investment on finding the solution. So, while you can be strategic about choosing the right market and problem (mostly by pivoting to different problems that your target market is facing, or solving the same problem for a different target market), most companies leave this up to luck. What should never be left to luck is the discovery of a solution for your market. This is where great product management principles and operations can make or break a startup, and much of the time this means prioritising the right solutions and finding the best way to tackle them.

Startup leaders are constantly facing decisions of whether they should build something themselves, or buy an out-of-the-box third-party solution. I believe startups should be biased against building anything inessential that doesn’t pose a legitimate opportunity to create a competitive advantage. In other words: only do what you’re positioned to do better than anyone else.

Products with product-market fit are products that have found an adequately sized market that they can be sold into. It’s more of a spectrum than a binary state — some products are more suitable for their market than others.

The best product teams I’ve worked with embrace the iterative nature of software development. Instead of committing to roadmap items, they commit to high-level, long-term goals. These goals are the focus of one or more teams for at least a year, and teams work towards these goals by tackling small chunks of work and constantly re-prioritising and re-thinking their approach.

In SaaS, your customers repurchase your product every month, quarter, or year. Your product should improve at this same pace. Renewals are so automated they feel like a passive process. But this is a false sense of security. Every time a customer pays, they should receive compelling value. This week, we explore why and how startups should operationalise their investment in software development.

While this is a word that often comes with negative connotations, I believe that great products, particularly in the B2B world, are usually very opinionated. They come with a strong view of how they should be used, and how the problem they are solving should be solved. These products differentiate themselves from the herd and disrupt incumbents by doing things differently. Many B2B SaaS products are simply automated workflows built from the opinionated views that you should solve that problem in this specific way.

I am an advocate for simple and collaborative methods for defining strategy for a team, department or company. Many strategy frameworks are too complex and while they may seem democratic (by embracing voting, for example), they usually lead to the middling harmony of sticking to the status quo. Instead, your collaborative process should encourage rigorous debate to overcome the mediocrity of concensus.

Most managers in early-stage startups think that chaos is inversely correlated with results. That is, they think that chaos breeds bad results and an unhealthy environment, while order breeds good results and a more harmonious environment. This perception is wrong.

As great as it would be to solve all problems with clearly defined processes and documented knowledge, the reality is that most organisational knowledge tends to be tacit. So, companies should factor this into their ways of working.

How much should competent people, confidently managing their responsibilities, meddle in the affairs of other teams they perceive to be dropping the ball?

People hate process, but process is crucial to scaling a businesses. Today, we explore the difference between good and bad processes, and ways to ensure startups can benefit from standardisation, rather than suffer.

As startups grow, leaders must decide how to structure their engineering teams. This week, we explore some principles for how to divide product development efforts across multiple engineering teams.

Most startups let their organisational structure organically develop as they scale, but organisational design can surprisingly greatly impact outcomes. This week, we explore how org design influences the way leaders and teams solve problems.

Leaders should create a fulfilling, enjoyable, and ergonomic workplace. But over optimising for comfort could lead to mediocre outcomes for your startup.

When I talk to founders, I often hear complaints about the pace of product development. “We used to move so quickly, but now we’ve barely delivered anything all year.” This week, we look at some of the most common causes of reduced software delivery.

Startups often neglect customer retention until churn becomes a severe problem. Successful early-stage startups tend to grow quickly, and growth hides churn. But churn is usually a big problem for startups before they notice it. Churn can seriously hamper growth at all startup stages, and when a startup grows without managing customer retention, it turns into a leaky bucket. Eventually, no matter how much you sell, churn will drag you down.

Most startups under-invest in their product documentation — when you’re busy with reactive customer support, it’s hard to justify proactive work like documentation. However, quality user documentation can dramatically reduce support team workloads and free up product development and customer acquisition resources.

While it’s common for product managers and engineers to look for underlying problems when they receive a feature request, teams rarely apply the same scrutiny to internal operational suggestions. This week, we explore how ideas for new processes can harm a startup.

Airbnb, Figma, and a few other high-profile tech companies have abolished the product manager role within their organisations. What can startups learn from this controversial move?

The best strategies and ways of working for early-stage companies can lead to chaos and quality problems for mature companies. Similarly, early-stage companies that adopt mature ways of working can move too slowly and burn through runway, when they should be finding product-market fit.

The negative impact of cognitive overload on productivity is well-established in research, but startup leaders rarely factor this into their strategy and operations. This week, we explore strategies to reduce cognitive load and improve startup productivity.

McKinsey claims that companies with great developer velocity achieve four to five times faster revenue growth, better operating margins, brand perception, talent management, and shareholder returns. This week, we explore the ways startup leaders can accelerate developer velocity.

When growth takes off, a startup could be on its fifth salesperson, fourth marketing manager, third customer success manager, and second product manager. This week, we explore how goals can set up startup employees for success.

Cognitive overload plagues startups. People frequently bombard you with problems, ideas, questions, complaints, and requests. One tactic that works for individuals and teams is to centralise requests and ideas into queues, which you later prioritise, schedule, and complete.

It is difficult for startup leaders to deliver major projects without neglecting their business-as-usual responsibilities. An operations team can solve this problem for startups by helping leaders with projects. This week, we talk about the best ways to set an operations discipline up for success.

A small, skilled, and effective operations team presents a startup with the opportunity to allow team leaders to focus on their business-as-usual responsibilities without the need to forgo business-changing improvements to how the business runs.

Great delegation is about handing ownership over to your team. Autonomy and accountability are the two sides of the ownership coin. Effective delegation requires a balance of these two forces. When startup leaders fail, it’s often the result of an imbalance between their autonomy and their accountability.

Sometimes, delegation leads to poorer results, and founders regret giving up certain areas of control. Other times, founders retain too much control over duties their team should own. While nobody can get this right every time, startup leaders can improve outcomes if they are strategic about delegation.

Startups can be flippant with cybersecurity, but even small companies are targets for attack. Worse, many startups never outgrow their poor security habits. This week, we explore a few ways startups can improve their security posture.

As your startup grows, responsibilities that used to belong to a single individual will be owned by teams and, eventually departments. This transition is where startup operations become critical. This week, we explore some of the rituals teams should adopt for continuous improvement.

Many early stage startup leaders struggle to accurately calculate the important SaaS-specific business metrics because their profit and loss statement isn’t well-structured for a SaaS business. This week, I’ve compiled some simple tips for aligning your P&L with SaaS norms.

As your startup grows, your team will get busier. More customers means more onboarding tasks, professional services projects, and support tickets. While this is a great problem to have, many startup leaders find it difficult to determine how many people they need in each team. Fortunately, some simple capacity modelling can simplify this process.

One thing I’ve noticed when talking to startups is how DevOps and product management are adopted to solve many of the same problems. While I think most companies will eventually require both, I’ve come to believe that it is more valuable to invest early in DevOps than product management.

While many product development leaders obsess over the positive habits their teams should adopt, they rarely pay enough attention to the downside of bad habits and over operationalisation.

Assembling your team is one of the most important responsibilities for any founder or leader. But, most startups I’ve worked with fail at effectively onboarding new staff, which can lead to false starts and failure.

Investing in product design (i.e., user experience and user interface design) can lead to fantastic outcomes for product development teams of all sizes because it reduces the number of iterations required to produce a great product or feature. However, most product companies approach product design in manner that excessively slows down the development of new solutions and blows out budgets. This has led to product designers being ostracised from many initiatives and decision-making processes/rituals. By embracing a DesignOps approach to product design, companies can instead move faster and get more done with less resources.

Despite all startups being resource-poor relative to what they are trying to achieve, many founders invest in solutions (e.g., specific product features, technology improvements, and internal systems/processes) that require effort beyond what is desirable from an ROI perspective.

While every company should approach this somewhat different, there are a handful of principles that apply to most product companies that I think you should consider.

Customer success is a critical function within the B2B software industry. It is typically staffed by customer success managers who are tasked with managing the experience of existing customers throughout their journey with the product, with the assistance of automation. Every B2B software startup eventually finds itself in need of a customer success function, but most struggle to spin one up without a few hurdles and misfires. This is because the focus of customer success is very broad, with diverse goals and roles required to succeed.

Assumptions around both expected value and effort required are usually wrong, often dramatically. The outputs of ROI algorithms can lead you astray if the inputs are incorrect, making prioritisation based on this method an exercise in futility. This is why teams should factor confidence into their ROI estimations, recalculate and reflect on ROI estimates after work has been completed, and assemble around long-term areas of focus where multiple hypotheses can be tested.

Today, software-as-a-service (SaaS) is the standard business model for monetising business-to-business software. In the SaaS model, software is licensed to customers through an ongoing recurring subscription (e.g., a customer might pay $25 per month for continued access) or another form of operational monetisation (e.g., transactional fees on application usage) which also includes customer services.

The best salespeople have great intuitions for which prospects are most decisive, and how to get access to better contacts. Everyone else wastes their time talking to people who will never buy, no matter how appealing they make it sound.

Startups should try to hire salespeople in pairs. This is particularly important when spinning up a new channel (e.g., launching in a new market, opening up a partner channel, or kicking off outbound sales).

Ambitious projects need ambitious goals, but bad KPIs can do more harm than good. This week, we look at some principles for defining measurable goals within a startup.

It’s easy to convince potential customers to take a risk on your product if you have irrefutable proof that it will deliver results.

Bottom-up SaaS is a sales strategy that targets individual users or teams within an organisation rather than the organisation as a whole. Given large organisations tend to buy slowly, especially when buying critical components of their digital architecture, this can accelerate growth for B2B SaaS startups.

Every startup needs a repeatable and sustainable sales model. This week, we explore the various strategies that work for SaaS products.

SaaS startups should aim for the recurring revenue they earn from each customer to grow over time. This week, we cover the foundational strategies for achieving recurring revenue expansion.

As B2B SaaS startups achieve scale, they gain the ability to achieve massive revenue growth by simply better monetising existing customers. This week, we explore some pricing strategies that make this type of revenue growth easy.

A self-service experience, including a free trial or freemium plan, is a cost-effective way to sell a product that is capable of selling itself. Many startup leaders underestimate how much work it takes to truly make this work, though. This week, we explore how to deliver a self-service SaaS experience, and how to decide whether this strategy for growth is right for you.

Sales model innovation is the most underrated challenge in conversations about product-market fit. Failing to experiment and innovate on the sales layer causes many startups to lose hope in markets, problems, and solutions with huge potential. Founders assume that because their solution isn’t selling, it must be an inadequate solution, or the market and problem they’ve identified are not big enough. Many teams expect product innovation to solve the product-market fit problem single-handedly, so they abandon anything that isn’t easy to sell, and burn their early-stage runway on product iterations. Often, some discipline and experimentation in the sales process could’ve successfully brought their early solutions to market. The problem with the typical framing of the product-market fit mental model is that it suggests that a startup will succeed so long as it finds a big problem and solves it. Unfortunately, it is rarely this simple. I encourage startups to adopt a disciplined, data-driven approach to marketing and sales to expand their criteria for product-market fit to consider the suitability of the sales model to the market and the product.

Teams can tackle increasingly ambitious initiatives if they learn to challenge risky assumptions with proofs-of-concept, research, and other forms of experimentation.

A common anti-pattern in the world of software development is the over-operationalisation of the research and development process. In moving away from traditional ways of working, companies will spin up long-lived teams, working to sprint cycles, but still find a way to cram an inordinate amount of upfront planning into the system, causing a significant amount of waste. This can feel like a big step in the right direction but often comes with very little benefits compared to the old way of working, as the way the team works doesn’t change.

A playbook I’ve used to describe the responsibilities of a software engineer for hiring and professional development purposes.

To make effective decisions when developing products, engagement with customers is critical. Building this into your way of working should be the priority of any product leadership. Along the way, data should be captured and analysed.

Many product managers don’t know how to prioritise technical work against new features. This is because they don’t have a deep enough understanding of the value of certain technical work. This week, we explore the ways to unify these often separate work streams.

In B2B SaaS, it has become the norm to charge extra for single sign-on. This week, we explore the argument for why SaaS companies should resist the urge to gate this feature.

Startups can be flippant with cybersecurity, but even small companies are targets for attack. Worse, many startups never outgrow their poor security habits. This week, we explore a few ways startups can improve their security posture.

One thing I’ve noticed when talking to startups is how DevOps and product management are adopted to solve many of the same problems. While I think most companies will eventually require both, I’ve come to believe that it is more valuable to invest early in DevOps than product management.

A common topic in product companies is the prioritisation of so-called customer-facing initiatives versus so-called technical initiatives (e.g., automated testing, reusable technical patterns, SDKs, automation, API-first services).

When an early stage employee can satisfy their own needs by simply succeeding in their role, you’ll achieve better results with less management overhead. When an employee needs more than you can give them, they will distract you from focusing on the most important things.

Every day, a great strategy fails in a startup because a leader underinvested in trust and relationship building or unnecessarily took autonomy away from individuals or a team. This week, we explore how Joseph Nye’s framework for soft and hard power can help startup leaders to motivate their teams and enact change in their organisation.

When growth takes off, a startup could be on its fifth salesperson, fourth marketing manager, third customer success manager, and second product manager. This week, we explore how goals can set up startup employees for success.

Great delegation is about handing ownership over to your team. Autonomy and accountability are the two sides of the ownership coin. Effective delegation requires a balance of these two forces. When startup leaders fail, it’s often the result of an imbalance between their autonomy and their accountability.

Engineers are the most important recruits for early-stage software startups, but many startups fumble their first engineering hires because they don’t understand what type of engineer they need. Even a great engineer can fail at a company they’re not suited to. Fortunately, there are a few broad principles that startup leaders can employ.

To build a startup, you need to build a great team. Recruiting can be tough for early-stage startups, though. This week, we explore how a strong employer brand can give startups a recruiting advantage.

As your startup grows, your team will get busier. More customers means more onboarding tasks, professional services projects, and support tickets. While this is a great problem to have, many startup leaders find it difficult to determine how many people they need in each team. Fortunately, some simple capacity modelling can simplify this process.

By being intentional about what types of experience are most important for each role, and considering team-wide capability rather than individual capability, leaders and founders can create powerful teams and nail the first and most crucial step of startup building.

Many leaders view their responsibilities as a list of leadership and management tasks they need to complete. This mindset ignores that the best way for a team to get most things done is through shared ownership and leadership. This week, we explore why leaders should delegate to shared responsibilities rather than individuals.

Assembling your team is one of the most important responsibilities for any founder or leader. But, most startups I’ve worked with fail at effectively onboarding new staff, which can lead to false starts and failure.

While every company should approach this somewhat different, there are a handful of principles that apply to most product companies that I think you should consider.

While losing staff to customers and partners is pretty common in B2B SaaS, I would advise against having any sort of non-compete/anti-poaching clause in your standard customer and partner terms. First of all, this is bad for your employees. As an employer, you should be competing in talent market by providing a great place to work, with fair compensation and benefits, not trying to lock them in with contracts they don’t have any influence over and may not even be aware of. If an employee wants/needs to leave, and their best prospects are with a partner or customer, it’s unfair to limit their options.

A playbook I’ve used to describe the responsibilities of a software engineer for hiring and professional development purposes.

A trend I’ve noticed amongst the most effective people I know is that many of them are keeping a personal knowledge base (which you could also call a personal wiki, a professional journal, or many other things). This is clearly a trend beyond my immediate network, given the glut of new tools at least partially designed with this purpose in mind (e.g., Notion, Craft, Clover, Roam Research, or Obsidian). I started my personal knowledge base in 2010 (using Evernote) and it has been incredibly valuable to me throughout my career, so it has been great to see this trend take off recently.