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The 4 factors almost every enterprise considers before approving software

Enterprise companies are often large, quite slow, and messy. Which means that the buying process for enterprise software is often large, quite slow, and messy. This process is vastly different to the world of B2C because rather than selling your product to just one individual, you’re selling it to an individual, who’s part of a team, that is part of an organisation with hundreds of people. This means more conversations, more layers, and more stakeholders.  Despite this, there is a lot you can do as a seller to anticipate and streamline the buying process – increasing the chances that a business will choose you over your comparators.

From being on both the buyer and seller side of enterprise software I’ve discovered that what seems like a lot to consider can actually effectively be broken down into 4 main elements that businesses typically look for when comparing solutions to find the right fit. These are the 4 elements you want to address on your website, elevate in your marketing, and continue to test messaging around to ensure you have the most effective narrative. They are the 4Ps of enterprise software:

Performance, Price, Profit, and Privacy.


Performance
simply speaks to how well your product works. What features are included, what benefits do they offer, how well it is designed, whether it feel like something you’d enjoy using. Part of assessing performance is also discovering how well the product works in tandem with other tools within the companies existing stack – ensuring your tool is effectively adding value to the whole ecosystem and not just operating in a silo.

Price is self-explanatory too. This addresses a focus on your business model, how much the software costs, and how these costs are broken down over time.

Profit is all about ROI and the extent to which this product will cause a saving and/or improve a process. Whether that be saving time, saving cost, improving capabilities etc. Within this prospects are also interested to see how other customers have benefited from your solution. So this is where customer stories, testimonials, and showcases come into play.

Last but by certainly no means least is privacy. This is an aspect often overlooked but is becoming an increasing more important part of the procurement process for Enterprises. Centre of attention is the question ‘How safe is my data?’ Customers want to know you’re a trustworthy partner and expect to see information about how their data is stored and processed. Now more than ever, with the rise of many tools being built entirely on AI, customers are adding an extra layer of scrutiny in this area to ensure their data is not being used for training models or sold to third-party organisations without authorisation.

The whole process tends to go something like this: In the first stage, it’s often your ICP (ideal customer profile) or someone near enough to it that discovers and evaluates your solution, primarily focusing on performance and profit as they determine whether this could solve their problem. Next, this champion might request a demo to learn more and share findings with their team or manager, where performance, profit, and price become the core evaluation criteria, often in that order of importance. If all goes well and the team are keen, the third stage involves organisational approval from multiple stakeholders who each scrutinise different aspects of the offering. Finance examines price and budget alignment, security teams evaluate privacy and compliance measures, whilst legal reviews contract terms and risk factors. Another level of approval to consider here is C-suite. Whether early in the buying process or later, CEO’s are now being actively more involved in the procurement process – scrutinising products and ensuring that the tech suite across the company is more consolidated and streamlined.

How you address these 4 main elements and the channels you use to communicate your value in each one is up to you, but ensuring you’re aware of these factors and constantly improving your messaging around them is vital to increase your likelihood of appeasing all stakeholders throughout the buying process. The framework's power lies in its predictability – by systematically addressing these apprehensions before they even arise, you can better anticipate objections, prepare targeted responses, and guide prospects through their buying journey more effectively than any other comparator they may be considering.

Why certain company events feel different

Company events are undergoing a fundamental transformation. The traditional model of packed auditoriums, keynote presentations, and rushed networking sessions is giving way to something far more intentional: experiences designed specifically to forge genuine human connections.

For me, putting on a good company event lies in being aware that people don't attend events primarily for information – they attend for transformation through connection. I’ve been to hundreds of events, and while content remains important, the most memorable and valuable experiences I’ve had happen in the spaces between formal presentations, in moments where strangers become friends, where casual conversations spark lasting relationships.

This shift demands a complete reimagining of event design and activities. Instead of defaulting to the familiar conference room setup with rows of chairs facing a stage, why not prioritise environments that naturally encourage interactions? Think round-table seating, club-house style venues that invite honest conversations, or even intimate outdoor spaces in nature. And instead of activities that involve passive consumption, why not focus on fostering active participation? Think interactive workshops and collaboration between participants to solve real business challenges. It’s not enough to end a talk and simply say to the attendees ‘alright, go off and network now’ – rather companies should shoulder that responsibility and purposely seek ways to weave connection as an important principle throughout the whole experience.

The details matter, because it is these details that people will recall, tell others about, and ultimately encourage them to come back for your next event. The potential ROI is massive. In a world where information feels abundant but genuine connection is said to be rare, the companies that lean into this shift will create experiences that foster a more intimate relationship with customers long-term. Helping them learn more and build better.

Looking for an example? Last year I attended a Figma London event hosted on the upstairs level of a coffee shop. No slide decks, no panels, no speeches. Just 3 Figma representatives, a group of people interested in design, and two barristers walking us through the art of coffee tasting. The interesting thing? Even though Figma didn’t necessarily ask us to speak about how we’re using Figma, as we tasted coffee blends from all across the world it naturally came up in conversation, as did many other topics around design and it’s potential future. The relaxed atmosphere was a catalyst for bonding, and odds are, everyone in the room left feeling more connected to those that they met than they ever would have at a corporate conference.

To summarise:

  • Connection trumps content – People attend events primarily for who they'll meet. The most valuable experiences happen through genuine human connections and meaningful conversations.
  • Design for interaction – Move away from traditional auditorium setups – shake things up, do something different, create an experience that people are likely to share.
  • Every detail shapes connection – Weave connection as a principle throughout the entire event, don’t just layer it on at the end. Make every touchpoint count and people will notice.

The untapped appeal of software gifting

Why don’t companies allow customers to gift software?

Today, B2C software is more personal than ever before. People are using some of these tools on a daily basis to earn, learn, create, plan, and play. So why is there no option for them to be gifted?

For some reason referral programs have become common practice and one of the optimal ways of boosting advocacy. But I’d argue that a gift goes a step further because they’re more useful in multiple situations. Picture this:

It could be the mentor who offers a 12-month Figma pro subscription as a gift to their mentee that is just getting started with product design. Or the friend who buys a 12-month Notion subscription for another friend that is starting out with freelancing and enjoys planning. Or the event host who offers a 12-month Cursor subscription as a prize to one of the guests in attendance. The list goes on. Each a much welcomed gifting option that shows you’ve considered the interests or even aspirations of the receiver.

This isn’t a new concept. When I was growing up, Apple gift cards were highly appreciated gifts because it meant that you could use those credits to add something personal and useful to your device, be it an app or song. Fast forward to today and Apple are still investing in gift cards – going beyond the previous realm of apps and songs and into being able to use your credits to buy anything on the Apple Store.

Whether this manifests physically as a small beautifully packaged gift or digitally as an interactive experience, that’s up to you and your finance team. But the returns are huge either way:

  1. Upfront cash for lengthy subscriptions.
  2. Potential of establishing or re-establishing a relationship with a user, who after the gifted subscription ends, is more likely to go onto purchasing a subscription themselves.
  3. A new expressive channel to bring your brand identity to life in a human yet creatively exciting way.

The third point highlights another important aspect of this strategy which is to own your own experience if feasible. Your own storytelling, design, and aesthetic. I’d avoid using a 3rd party gift card marketplace because the utility isn’t the only thing people are buying, but also the experience and feeling it offers.

Don’t believe this is something people actually would utilise? 10 minutes of searching online will tell you otherwise:

Does every campaign require a tagline?

Require? No. But that doesn't mean taglines aren't important levers that enhance the longevity and effectiveness of your campaigns. For most startups and scaleups, campaigns are rarely integrated. This means when marketing collateral is created, it's often distributed sporadically across different channels with no connecting thread to tie the content together. Yes, the word gets out, and yes, people may engage with it. But there's no story. No narrative that audiences can latch onto. No theme to share, and often no depth.

Taglines aren't just words – they're platforms that can traverse multiple channels, creating a compelling yet coherent narrative for customers to connect with and share. Not having a tagline costs you time and money because each time you're creating a new narrative rather than building on an existing one. Starting with a tagline gives you a foundation to build upon, and from there you can consider how that line, narrative, and direction manifests across multiple channels.

To illustrate this as an abstract diagram, it might look something like this:

The channels will be up to you, but the same principle applies. You use the tagline as a way to inform the creative you produce.

Looking for examples of this in action? In 2021, Dropbox released a new brand campaign with the tagline 'For all things worth saving', acting as a creative platform for them to showcase how individuals from all walks of life utilise Dropbox to store the files and memories that matter most to them. This platform was about the product, sure. But it felt different. It felt personal, emotive, and frankly un-SaaS-like, for all the right reasons. The campaign manifested across multiple channels, including a hero video shared on YouTube, billboards, a website takeover, and more. Through this platform, Dropbox was able to nurture a closer relationship with their community (by amplifying personal stories), reach new audiences, and re-establish what they want to stand for as a company.

Dropbox wants you to rethink your files in a new collaboration with  Instrument
Dropbox: For all Things Worth Saving — Dom King
Dropbox wants you to rethink your files in a new collaboration with  Instrument

So, in conclusion:

  • Taglines are not just words – they're platforms that elevate the stories you tell.
  • Integrated marketing campaigns supported by taglines save you money and time while enhancing brand consistency.
  • Not every marketing initiative requires a tagline or platform – sometimes reactivity is the goal over longevity. But I wouldn't recommend making this the default.

Billboards never went anywhere

Billboards work when you use the canvas as art, not a way to return investment (even is that is the end goal). I say this because If you overfocus on ROI over the art then you end up making something cold, functional, and unengaging. Something people are unlikely to share. Effective OOH doesn’t just occupy space in a location, it complements it, morphs it into some interesting, something you want to look at at and re-look at. Something you want to take pictures of and tell others about. The truth is you’ve got six seconds, or less. Six seconds to entertain, six seconds to excite, six seconds to intrigue. That’s why you often see companies relying on more than just one ad and instead utilising multiple to create a takeover that elevates the experience. But whether you use one or multiple, the same goals apply: entertain, excite intrigue.

All of that said, I’m not naive, billboards aren’t cheap and there are growth targets to meet. So how do you measure attribution for this amazing art you plan to create? Well, it really comes down to awareness and engagement. Awareness can be broken down into two sub categories: discovery/re-discovery and perception. Through a billboard people can discover your company exists, or be reminded that it exists. It can also cause them to instil or upgrade the perception they have about your company, its style, and ethos. If you’ve interested viewers enough you may then turn this awareness into engagement – people actually checking your website, sharing your post on social media, or booking demos. High awareness (from impressions), and high engagement (from clicks) – that’s what an effective OOH campaign looks like.

Part of achieving this though isn’t just based on what content you include on your billboard but also it’s location. Assuming that your best bet is to place a large billboard in the place with the most footfall is costly. More effective, is choosing to place your billboard in a location that is likely to garner the most impressions from your target audience. Perhaps outside a conference they’re likely to attend, beside offices where their companies are stationed, or not too far from the food market where they’d typically pass for lunch. And I know I’m talking about billboards here. But OOH can manifest in multiple different forms, such as posters taking over a wall, digital pop-ups, or even installations (more on this in a separate post).

As technology continues to evolve, OOH has the potential to get really exciting. Whether it’s advancements in AI, augmented reality, or virtual reality, brands will have at their fingertips more ways than ever to engage audiences, create compelling experiences, and ultimately elevate their storytelling. So let’s make art (and hit those targets in the process).

In conclusion:

  • Billboards aren’t dead for SaaS.
  • You’ve got six seconds or less – entertain, excite, intrigue.
  • Content is important, but so is location.
  • The future of OOH is exciting.

Looking for examples of SaaS companies that have done it well? Look no further:

Notion:

Mailchimp:

Ramp:

The Simple Act

The simple songs are recalled the most.

The simple ads connect with the most people.

The simple products have the most users.

Simple is not boring. 

Simple is considered. 

Simple is timeless.

Simple is universal. 

Simple is accessible. 

Simple is void of clutter.

Simple speaks for itself.

Some people think simple is less, but it’s actually more:

More thought.

More hours.

More care.

More revisions.

An experience void of simplicity is noise.

Noise is easy to make; whereas simplicity is more challenging to maintain.

But those that maintain it cut through,

and often silence their noisy counterparts.

Companion Planting

Companion planting is a term often used in gardening. 

It refers to the act of sowing certain types of plants in close proximity, so they may benefit from each other's unique offering, and thus grow sustainably. Giving and receiving in tandem.

An example of this is the ‘3 sisters': corn, bean, and squash plants. When planted close together:

  • Corn offers a physical support structure 
  • Beans provide nitrogen
  • Squash covers the soil to prevent evaporation and weed competition 

Ecosystems thrive when plants collaborate rather than compete.

And this is not dissimilar to the dynamics of a brilliant team or community.

Everyone has something to give. Therefore, give, and provide the platform for others to do the same.

Speaking to Customers

When was the last time you met with your customers face to face?

Not learning about them through a trend report, or analysing their usage behind a screen. 

But hearing them share their experiences in first person, noticing the micro-interactions displayed as they use your product, seeing the emotion expressed as they explore the journey that you crafted.

Most of us may have seen the recent articles about Airbnb’s growth since shifting to a model focused on brand building. But beyond campaigns and design refreshes. This approach was fuelled by the fact that they maintained close contact with their community through a willingness to meet and hear from the individuals that form it.

In a world where everyone wants to be heard, positioning yourself as the brand that listens becomes a key distinguishing attribute.

Regenerative Business

Is your business regenerative?

The definition of regeneration is to regrow (new tissue) after loss or damage.

It’s a great attribute to have.

One that signals a sense of longevity, sustainability, and resilience. 

For this to happen on a regular basis, there must be a process in place to facilitate it.

There must be an intent to nurture the new

And a willingness to recognise its importance to the future.

So ask yourself:

Does my business act as fertile ground for growth?

Is my business set up to undergo renewal, should it be necessary?

Are we doing enough today to develop our tomorrow?

The 8 Star Experience

A 5 star experience is the expectation.

That just means the product you made performed as it should.

How many times have you given an Uber driver 5 stars for simply picking you on time and dropping you off at your destination?

The transition from a good experience to an exceptional one starts when you begin to consider what a 6,7, and 8 star offering looks like.

That should be the bar, or rather the platform.

Ultimately this takes patience.

It takes empathy.

It takes a willingness to dig a little deeper, go a little further.

Something not every brand is willing to do.

Doing digital vs being digital

Many companies do digital, few are actually digital-first organisations; despite the claims.

To be digitally-led is to see technology as a key driver in achieving your strategic aspirations. Developing products that leverage it’s capabilities to deliver incremental impact for customers, long-term.

It is to constantly operate in beta mode – fostering a culture of learning that permeates throughout the business.

And to ensure cross-functional connections are seamless, with each part of the business maintaining an appreciation for the opportunities offered by technology.

Ultimately, operating as a digital organisation shouldn't be an initiative solely governed by the CTO or CDO. It’s an ambition that should be shared throughout the whole company, and shape every decision that you make.

What to do and what not to

A key element of being efficient is minimising waste.

This is often overlooked.

Though it is important to highlight what you should do.

It is just as pivotal to identify what not to do and what to stop doing.

Clear the road, make room for what matters, and avoid unnecessary pivots.

What's our why?

Hold the problem you’re solving tightly, hold the user tightly, hold the solution you’re building loosely” – Michael Seibel

Building for a fleeting 'why' is like aiming at a moving target.

What [we’re building] and how [we build it] is subject to change, it’s inevitable.

But why we’re doing it shouldn’t.

That’s what we’re solving.

That’s our North Star.

If we agree that the why should remain consistent, ensuring that it feels right to start with becomes all the more important.

People and Spaces

For most brands, a new store is simply another touch-point.

But for those that live in the area, it’s much more.

The most impactful retail locations put the life that surrounds the building before it’s infrastructure,

positions the brand as an extender of the local culture already fostered,

and goes beyond procurement to provide a hub that gives more to the community than it takes.

“First life, then spaces, then buildings…” – Jan Gehl (Danish Architect)

Customer Service

The Genius Bar isn’t just a nice to have for Apple, it’s an integral part of their brand experience that says to the customer  “we hear you, and we care". It mitigates the risk of purchase and fuels customer satisfaction.

Often, we attribute the affinity for companies like Apple and Nike to the great work they do pre-purchase. But don’t always speak about the positives of their post-purchase experience. For most brands the service is great, until you have a query, until your product acquires a fault, until you have to make a return. Then you begin to see how much they really value customers, or rather how much they don’t.

Efficiency and Direction

The prerequisite for efficiency is direction. Hence why strategy is so important.

Once you have a plan in place you can run with conviction;

reassured in the fact that you're competing in the right race.