Why scaling is less linear than it looks, plus product-market fit, fundraising readiness and knowing your investor
Jamie Akhtar · CyberSmart
Published September 1, 2022Jamie Akhtar, CEO and Founder of Cybersmart shares:
- Achieving Product Market Fit
- Dealing with challenges: pandemic, war, and a looming recession
- Raising: staying ready & know your investor
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Jamie Akhtar recounts the path to building CyberSmart, including the less predictable realities behind apparent linear growth. He discusses surviving difficult market conditions, operational tools, and the role of financing in the company journey.
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“forward so that's kind of the core message I want you to take away from today so here we go starting out me and my co-founder 2016 um as you might have guessed I'm from London so staring in London Sky every every founder looks like this you know so like like just gazing into what you could achieve Etc no longer my co-founder come on to talk to that about uh in a few minutes anyway but essentially it's about like looking out starting out with like”
“times once you've reached these days so this is kind of like your your first job as a Founder is getting to to that stuff so”
“those two two graphs and just stay positive I think is is another big takeaway um like when you're you're one person when you're five people 50 people 500 people just stay super positive so three three quick tips last bit of this section um and things that I do personally so this is the kind of wrap-up of my personal stuff um so number one laser focused I mean I'm pretty sure all of us have this like super Focus anyway you need it to be a Founder but just be identifying stuff”
“and telling them it's going to be fine but like just understanding that they're going to have a human reaction to this stuff as well I think is is super important um so we ended the year like 2021 on a on a real high we'd hit our goals it was great and then obviously the Ukraine crisis happened that directly impacted like five of our team members so who were in Ukraine and it had like shock waves throughout the whole company so we had to like figure out how how do we support them so we basically just said”
“um a couple of things we've done with the team as well Freedom days in the UK we had like severe lockdowns like three months you couldn't leave the house type thing and we had like this Freedom Day we gave everyone the day off took them on a boat um so that was great you know obviously no productivity but like massive long-term gains um doing a retreat we had about this yesterday as well like just if you're especially a remote team like get everyone away once a year somewhere you can do it for about 2k a person”
“Achieving Product Market Fit”
“PMF: We had huge gaps”
“Above all … take others on the journey”
“Early: Angels, Later: VCs + Debt”
“How to survive thrive as a founder”
Video
How I hit $3m in ARR - Slide Deck
Jamie Akhtar is the CEO and co-founder of CyberSmart. Jaime is a is a veritable titan of the cybersecurity industry. From cutting his teeth in New York serving as CTO for investment firms and gaming companies, to turning his attention to the underdogs, Jamie has a refreshing and unique take on the industry at large.
Jamie Akhtar · CyberSmart
Jamie Akhtar · CyberSmart
Ari Salafia · Taxtaker
Becca Kay · Dingus and Zazzy
Ben Carpel · Galleon
Brad Miller · AwarenessTech
Each slide with a short explanation of what it shows. Open the slide text for its exact wording.
75 passages
Jamie Akhtar CEO, Founder of Cybersmart How we hit $3m in ARR Founder500, Sept 2022 … during a pandemic, a war and a looming recession
The talk moves from finding product-market fit to handling setbacks and scaling a company. Its route includes pandemic pivots, war and recession planning, fundraising, objectives, team growth, and revenue.
Over the next 20 minutes: You have one job I’m going to show you Starting out Dealing with challenges Scaling up Achieving Product Market Fit Let’s take a reality check Pandemic pivots War and fallout Bracing for a recession Raising: staying ready & know your investor Delivering: Objectives and Key Results (OKR) Growing: your team and revenue
This section introduces the speaker’s early founder journey and the work of getting a company started.
Section 1: Starting out My journey
Early startup work requires founders to understand their own focus and approach product-market fit in both theory and practice. The section also sets up a reality check on startup outcomes and hindsight.
Section 1: Looking within Starting up is simple, right? Where you need to focus Getting to know yourself Your Job Product Market Fit Reality Check The theory The practice Startup stats Hindsight is a wonderful thing
A 2016 photograph of the speaker and co-founder accompanies the question, “How difficult can it be?” It captures their early optimism before the work of building the company.
How difficult can it be? Me and my co-founder, 2016
The founder’s central job is to build a strong product that solves a significant problem.
Your one job… Build a great product that solves a big problem
Building the product alone is not enough: the founder also needs to raise money and hire good people.
Your one job… Build a great product that solves a big problem Raise money and hire good people
The founder’s role includes setting direction, raising money, and hiring well. A Venn diagram frames the “sweet spot” as the overlap between personal strengths and what the world needs.
Your one job… Build a great product that solves a big problem Raise money and hire good people Set the vision, raise money and hire good people
The founder’s job grows beyond product, vision, fundraising, and hiring to include whatever is needed to reach the goal.
Your one job… Build a great product that solves a big problem Raise money and hire good people Set the vision, raise money and hire good people Do everything that needs to be done until you achieve this
The slide warns that achieving product-market fit is not a straightforward process, puncturing the expectation that founders can simply follow a formula.
How we achieved Product Market Fit Spoiler alert: it’s not possible
CyberSmart’s revenue rises across the chart from $37,974 in 2018 to $3,059,428 in 2022, with each displayed year higher than the last.
CyberSmart Revenue Growth
The first step is an insight and an early concept pitch. The timeline places this initial exploration in 2017.
CyberSmart Revenue Growth Step 0-1: Hunch and Insight Pitching the first concept 2017
The early product moved through a minimum sellable product and repeated iterations. The slide emphasizes shipping before the product feels fully polished.
CyberSmart Revenue Growth Step 2-3: MSP and Product Iterations If you’re not embarrassed when shipping your first product, you waited too long 2017
A photograph of the founder presenting illustrates the idea that each product refinement brought the company closer to product-market fit.
Every refinement brought us closer to PMF
The timeline traces CyberSmart from its 2017 founding and early team through an initial funding round, disruption, and later product and team milestones. It shows progress arriving through several stages rather than one launch.
Our early journey Disaster strikes Struggle and strife Getting traction but the challenge is just beginning
The early product-market-fit starting point is a simple cybersecurity landing page. It presents a focused offer before broader platform positioning.
PMF: Where we started
CyberSmart places its platform between endpoint tools and several surrounding groups, including service providers, technology partners, insurers, larger businesses, industry bodies, and small businesses.
PMF: Where we saw ourselves
A maturity matrix compares the current state with realistic and optimistic targets across product strategy, prioritization, customer feedback, implementation, and product quality.
PMF: We had huge gaps How we used to look!
The onboarding diagram connects account creation, a platform tour, and setup to the steps customers take to secure employees and devices.
PMF: So we mapped out journey
A recurring decision process evaluates and prioritizes ideas, then either turns them into backlog items or discards them.
PMF: We asked: will it move the needle?
The backlog process moves selected work through Jira, feature specifications, wireframes, design, and sizing, with reprioritization along the way.
PMF: We groomed the backlog, again and again
The development cycle links planning and a sprint backlog to coding, review, staging, QA, acceptance, demo, production, and retrospective.
PMF: We shipped product relentlessly
People, processes, and technology feed a risk and recommendation engine. It turns those inputs into human guidance and machine integrations that can be used by other systems.
PMF: Where we ended up
Two customer questions gauge product-market fit and satisfaction. The slide highlights 40% as the benchmark for how many customers would be very disappointed if they lost access.
How we measure Product-Market Fit We asked all our customers 2 questions: 40%: How would you feel if you could no longer use CyberSmart? A) Very disappointed B) Somewhat disappointed C) Not disappointed CSAT: ‘How would you rate your overall satisfaction with the CyberSmart platform?’
A weekly confidence index tracks progress on three objectives and eight key results during Q4 2020. The plotted values fluctuate around four, giving the team a recurring signal to review.
How we measured team confidence (Q4 2020) Every week we asked : how confident are you?
The installation chart climbs from a handful of product installations to tens of thousands across the 2017–2022 period, illustrating the company’s scaling curve.
CyberSmart Revenue Growth Step 4+: Growth and Scale! Actual product installations 2022
A rough, uneven startup trajectory gives way to a smoother scale-up curve, illustrating that growth becomes more predictable only after early uncertainty.
In reality: it’s non-linear
The slide compares product-market fit to a liquid rather than a solid, suggesting it shifts with circumstances instead of staying fixed.
That’s because PMF is not a solid, it’s a liquid
This section turns to the challenge of beating the odds and keeping a startup moving through difficult conditions.
Thriving as a startup: How to beat the odds
The cohort chart shows fewer startups continuing at each successive stage from seed through later funding rounds, emphasizing how many companies fall away.
How comforting…
A review of failed startup autopsies ranks team gaps and an unsuitable business model among the leading reasons for failure. The adjacent objective example shows how a broad goal can be expressed as a measurable partner-growth target.
Real world data … avoid these pitfalls
A team photograph anchors the message of maintaining positivity as the company grows from five to 55 people.
Staying positive, from 5 to 55 people
A laser image represents the need to concentrate effort on a narrow set of priorities.
Beating the odds… be laser focused
An armadillo image serves as a visual metaphor for developing resilience while facing startup challenges.
Beating the odds… build resilience
Penguins gathered at the edge of an iceberg illustrate the idea of taking the team on the journey through uncertainty.
Above all … take others on the journey
A collage of team activities pairs the difficulty of starting a company with the reminder to enjoy the experience along the way.
Starting up is hard - have fun on the way!
This section focuses on guiding a team through major disruption and uncertainty.
Section 2: Leading
The agenda names pandemic disruption, war, and recession as leadership challenges. It calls for adapting plans, building a strong operating system, supporting the team, and preparing for downside while staying hopeful.
Section 2: Leading others Pivot everything Build a rocket factory Support, support, support Through challenging times PANDEMIC WAR RECESSION Direct impact Indirect fallout The long tail Plan for the worst, expect the best Default dead, alive, thrive Don’t lose sight of the end game
The 2020 pandemic changed the company’s outlook and extended the time needed for scalable product-market fit. The response is to work with agility and accept uncertainty.
Pivot everything Get real and prepare the team
For Q4 2020, the company narrows its strategy to two priorities: move beyond certification toward product-market fit and maintain or scale the existing business.
It’s time to switch gears and prioritize building an incredibly valuable business. The only way to do that is through hyper-focus. Next quarter will contain a limited set of objectives, focused on just two areas: Find product-market fit for SaaS beyond certification (PMF) Maintain and scale our current business (BAU) As a result, we’re re-aligning and challenging ourselves for a very productive Q4 2020. Strategy - where are we heading
A rocket image frames the task of building an organization that can repeatedly launch products and deliver results, with leadership helping the team coordinate the work.
Explaining through analogies
The guidance encourages leaders to pause, reflect, practice gratitude, switch off, act kindly, and support wellbeing while finding a positive angle in difficult circumstances.
We’re all human Show your team you actually care
A collage around 2021 and 2022 accompanies a prompt to identify things to feel excited about. The slide is an invitation to look for positive possibilities.
21 things to be excited about in
Hands form a knitted peace sign, conveying a message of unity and support.
The slide describes practical and financial help, daily contact, and support for team members who need to relocate during a crisis.
‹#› We have extended our full support (time + resources) to assist with those wishing to relocate We remain in daily contact and constant review of the developing situation We will continue to support our team, however possible, both financially and practically
The example “bad” slide states that the pandemic, war, and recession harmed the global economy and increased uncertainty and reduced confidence.
The bad Actual slides
The example “good” slide balances external challenges with strengths: a capable team, sound unit economics, and supportive, well-capitalized investors.
The good Actual slides
This section introduces practical tools for raising capital, delivering results, and growing the company.
Section 3: Your Tools
The toolkit groups advice into raising, delivering, and growing. It covers knowing investors and alternative capital, setting strategy and objectives, sustaining momentum, and developing the team.
Section 3: Your toolkit Are your backers pulling you down or pushing you up? Know your investor Alternative sources of capital Getting equipped for success RAISING DELIVERING GROWING Set the strategy OKRs Maintaining momentum Investing in people
This transition introduces the founder’s explanation of using debt to fund growth while limiting dilution.
The real terms we got from Founderpath Why we chose debt over equity
After reaching $3 million, the company sought growth capital without giving up more ownership. It compared more than ten providers, drew down $650,000, had another $1,500,000 available, and describes a two-year payback with a 9% discount.
CyberSmart Revenue Growth We Hit $3m and wanted to scale But didn’t want to dilute the cap table to scale….. 2022 We checked 10+ providers and Founderpath came out on top: Drawn down $650,000 and have another $1,500,000 available 2 year payback 9% discount rate Under 7 days from signup to wire
The slide calls the funding process the fastest and easiest capital the company had received. Its product screenshot illustrates a funding offer and repayment details, without requiring the small interface figures to be read.
The fastest, easiest capital we ever got
A score of 860 is shown for July 13, 2022. The slide says that as the company’s score improved, it unlocked better financing terms.
CyberSmart Revenue Growth …. As our score improved, we unlocked better terms 2022
A KPI dashboard tracks recurring revenue, growth, average revenue per customer, customer churn, and retention over several months. The measures help the team monitor the economics of growth.
KPI’s help us stay focused on hitting world class unit economics
This transition starts a set of practical fundraising tips focused on cash and investor readiness.
Quick tips Raising: Cash
The cap table slide highlights a mix of backers, early angels, later venture investors, and debt, with 48 participants counted across the cap table.
Backers Early: Angels, Later: VCs + Debt 48 and counting on the cap table!
The comparison spans friends and family, angels, venture capital, corporate venture, and private equity. It contrasts cheque size and value-add with ease of closing and investor expectations, emphasizing that capital sources differ.
Friends & Family Angels (most helpful) Venture Capitalists Corporate Venture Private Equity What we learnt Biggest differences ⬇️ Cheque size ⬇️ Value add ⬆️ Ease of closing ⬆️ Expectations Not all cash is created equal!
This transition introduces practical guidance for executing company objectives.
Quick tips Delivering: Results
A simple strategy links building the product to reaching customers at scale and delivering a great customer experience, with growth connecting the steps.
Keeping it simple: actual drawing From 5 years ago
The Q3 2022 objectives are to increase customer value, grow monthly recurring revenue from £290k to £360k, and make customer experience a way of life.
2022 Q3 - Business Objectives Objective 2: Grow company MRR from £290k to £360k Objective 1: Increase customer value of CyberSmart products Objective 3: Customer eXperience (CX) as a way of life! ‹#› “Don’t find customers for your products, find products for your customers.” - Seth Godin “To Infinity and beyond ” - B Lightyear “We are now primed to fully embed our CX obsession in all we do” - Jamie M
Research and innovation gather customer insight, which informs product, UX, engineering, and QA work. Improvements are then tested through customer outcomes and further feedback.
How? Through understanding our customers and building a better product Objective 1: Increasing Customer Value ‹#›
The objective is to raise company monthly recurring revenue from £290k to £360k. The diagram splits customers into partner and direct channels, each with its own recruitment and growth steps.
Customers Partners Direct Maximise Recruit Grow Recruit & activate 1 2 3 ‹#› Objective 2: Grow company MRR from £290k to £360k
Four key results focus on customer expansion, timely communication, a customer experience index, and personalized interactions. The circular diagram describes customer groups moving through evaluation, adoption, and advocacy.
O3KR1: Customer ExpansionOptimise and monitise our partner pool with a focus in CX and revenue expansion O3KR2: Customer CommunicationCommunicate at the right time, in the right way to the right people! O3KR3: Customer Experience Index Embed customer health into our business by providing our business with a MVP health/ satisfaction/sentiment indicator. O3KR4:Contextual Customer Experience Drive a contextual and personalized WOW when a ‘moment of truth’ presents itself CX ‹#› Objective 3: Customer eXperience (CX) as a way of life!
This section shifts from execution and customer experience to building a team that can sustain growth.
Quick tips Growing: Your Team
A lone palm tree on a small island illustrates the reminder that founders need other people around them.
Answer: no one is as island Are you an island?
The slide pairs a photograph of a team member working with the prompt to focus on culture when work is difficult.
Work is tough so… Focus on culture
A team photo accompanies the description of what the company’s culture means in practice: getting work done while keeping a positive attitude.
We say: we get stuff done with a smile on our faces For us that means
A team outing on a boat is presented as a “freedom day” that brings colleagues together to recognize small wins.
Our “freedom day” to unite the team Celebrate little wins
A group photograph at an offsite venue supports the recommendation to hold a retreat, especially for a remote-first team.
Invest in togetherness Especially in a remote first world Do a retreat
This transition introduces the outcomes of the practices discussed in the talk.
What have we achieved from implementing this Finally… the results
The revenue chart traces growth from $40k in 2018 to $3.2m in 2022, with a continuing upward trend after that point.
CyberSmart Revenue Growth
The slide’s revenue curve marks $4.5m as today’s level and projects further growth to $12.2m by 2024. It closes the story with an expectation of continued expansion.
The founder motto: We’re just getting started Today: $4.5m
The recap returns to the talk’s three themes: finding product-market fit and reality-checking the startup, leading through disruption, and using tools to raise, deliver, and grow.
Over the last 20 minutes, I showed you: You have one job How to survive thrive as a founder Founder to CEO Leading through… Your Toolkit Achieving Product Market Fit Let’s take a reality check Pandemic pivots War and fallout Bracing for a recession Raising: staying ready & know your investor Delivering: Objectives and Key Results (OKR) Growing: your team and revenue
A collage contrasts long-distance and sprint runners with the message that building a company is a marathon, not a sprint.
The closing card thanks the audience and identifies Jamie Akhtar as CyberSmart’s founder and CEO. It closes with the company branding and an invitation to learn more; contact details are omitted.
September 2022 Jamie Akhtar CEO, Founder of CyberSmart Exclusive F500 pre-reg: cybersmart.com