Advice & resources

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.

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.

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.

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.

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.

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.

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.

To effectively make decisions, founders and product leaders need to be aware of which of these two mindsets they should be employing. Applying feedback intended for mature businesses to your small-and-scrappy startup can be a real distraction, while applying feedback intended for businesses still searching for product-market fit to a scale up can lead to an unstructured, chaotic environment. For example, many early stage companies agonise over things like technical debt and employer brand when, as important as these things will soon be, they are currently an unnecessary distraction.

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.

Two belaboured topics in the product development community are the operationalisation of software costs (i.e., the SaaS-ification of everything) and the movement from project teams to product teams. I think what many product professionals miss is the deep connection between these two movements, and how this impacts the importance of the latter transformation for all SaaS companies.

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.

Scope cutters can get a bad rap. We've all experienced situations where a team, under the pressure of a looming deadline, is forced to remove functionality from their upcoming delivery and the result is an unworkable feature that does not meet user needs. So, it's understandable that when the scope of a feature is cut during the development cycle, this is often met with cynacism and disappointment.

To meet and exceed market expectations, feedback is crucial. The nuances of how you collect feedback, such as the audience you target and the questions you ask, can have a significant impact on eventual outcomes. One seemingly trivial decision that can significantly influence outcomes is how you ask stakeholders to score an experience. This is often done using a five- or ten-point scale, sometimes represented by numbers, stars or words.

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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.

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.

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.

When starting an initiative, it is important to focus on the desired outcome before jumping to solutions. A simple first step towards becoming an outcome-focused organisation is to change how you define initiatives. Many companies define initiatives in an output- or idea-centric manner, where the focus is on the specific desired scope. This can lead to confusion around why we're actually tackling an initiative. It also limits us to only think about the suggested idea, rather than alternatives. Better and simpler ideas are often waiting to be found.

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.

When faced with a choice between two implementation paths, in their relentless pursuit of delivery momentum, many teams can fall into the habit of choosing the path of least resistance. While I'm an advocate of reducing scope when it doesn't jeopardise intended outcomes, always choosing the easiest pathway for implementation can cause problems in the long-term.

Below is a playbook I've used to describe the responsibilities of a product manager for hiring and professional development purposes.

When starting an initiative, it is important to focus on the desired outcome before jumping to solutions. A simple first step towards becoming an outcome-focused organisation is to change how you define initiatives. Many companies define initiatives in an output- or idea-centric manner, where the focus is on the specific desired scope. This can lead to confusion around why we're actually tackling an initiative. It also limits us to only think about the suggested idea, rather than alternatives. Better and simpler ideas are often waiting to be found.

When starting an initiative, it's important to focus on the desired outcome before jumping to solutions. By focusing on the problem to be solved, we can ensure all ideas are considered and that we are all working towards a common goal.

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 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.

Below is a playbook I've used to describe the responsibilities of a product manager 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.

Over the past decade, many of the big software suppliers in ecommerce have been moving towards an "all-in-one" strategy, with seemingly everyone trying to become the one-stop-shop for retailers (i.e., inventory management systems adding order management capability, order management systems adding inventory management capability, marketing apps adding storefront functionality). The result has been the emergence of broad platforms that have a lot of features, but don't do anything great (jack of all trades, master of none; wide but not deep).

As social media platforms like Instagram and Pinterest finally expand into social commerce, much has been said of the looming threat these platforms present to the likes of Amazon and eBay. An examination of how these social platforms differ from the incumbent marketplaces suggests that social commerce is a bigger threat to traditional e-commerce platforms than it is to Amazon or eBay.