Understanding Sales Cycles

Stop trying to enter defence without understanding what it actually is. This may sound harsh. It is meant to be. I keep seeing the same pattern across startups, manufacturers, consultancies, ICT providers, innovation teams and everyone else who try to enter defence. The ambition is there. The decks are polished. The language sounds right. But the understanding is not. Defence is not just another market you “enter”. It is not: a product you decide to sell a single procurement to win a pipeline you build like in commercial markets a fast adoption cycle And it is definitely not a place where “if it works here, it will scale elsewhere”. What is missing, over and over again, is basic grounding. Not in theory. In reality. If you want to operate in defence, you need to understand: 1. The environment Systems must work: - when GPS is denied - when communications are degraded - when data is incomplete or false - when the operator is under stress If it only works in ideal conditions, it is not a defence capability. 2. The user Your end user is not procurement. It is the operator. Different mission = different constraints, risks, decisions. If the operator does not trust your system, it will not be used. 3. The system Defence is not one buyer, one role, one path. It is a combination of: - states - primes - integrators - operators - supply chains You are not selling into a line. You are entering a system. 4. The timeline Adoption does not happen in quarters. It takes years. Not because defence is slow but because failure has real consequences. Trust must be built: - technically - operationally - organisationally 5. The reality of integration Your solution does not exist alone. It must: - integrate into legacy systems - survive electronic warfare - function in degraded environments - fit doctrine and command structures If it cannot integrate, it will not deploy. 6. The market There is no “global defence market” in the way many assume. There are: - different doctrines - different procurement systems - different political contexts - different industrial ecosystems What works in one country often fails in another. And this is where most attempts fail. Not because the idea is bad. But because the entry is built on assumptions instead of understanding. Defence is not a place where you start with: “We have a product.” It starts with: What problem are you resolving and to whom? Where do we play? In which role? In which system? .... And are we trusted as persons as TRUST is the foundation and personal. Only then does the product make sense. Because in defence, buzzwords don’t matter. Survivability does. Integration does. TRUST does. #DefenceInnovation #DefenceTech #DualUse #NoBuzz

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

Every sales leader I talk to at the moment is struggling with some version of the same issue. The symptoms are different, but the underlying cause is the same. - Sales cycles elongating - Deal slippage - Prospects not showing up to meetings - An uptick in ghosting - Poor forecast accuracy - A drop in deal volumes - A drop in conversion rates What's actually happening out there in Buyer land? I've been delivering win-loss reviews for B2B companies around the world since 2011 and I'm seeing buyer behaviours I've never observed before... Let me break down some of them quickly for you and share some guidance on how to use these lessons to your advantage: Trend #1: Risk has jumped up the decision tree in order of importance, to the very top of the list for many clients, even more so when it's a new vendor. Action: Go deeper on risk in your discovery conversations, recognise that risk is both organisational and personal...find ways to better manage, mitigate and share risk with your clients...Be the low risk option. Trend #2: Value for Money, Responsiveness and Cost are consistently selected as the most important decision criteria by many clients. Action: Responsiveness should be an easy one to get right, but many sellers are stretched too thin right now...do less, but do it better. Trend #3: Change in Strategic Direction is the most frequently cited reason for customers coming to market for a new solution at the moment. Action: Try to reverse engineer this reason, to understanding what caused this change in direction and what it actually means for the business. These are your keys to the kingdom, when building a rock solid business case. Trend #4: Feedback from Peers and Colleagues has emerged as the most trusted information source for almost all respondents. Action: Case studies and customer references are losing their luster...find ways to tap into the trust which prospective clients have in their own peer network, as a way to unlock deeper connections and build trust. Trend #5: Customers are demanding more detail in the proposal documents, tender responses and business cases which they are receiving. Action: Put in the work, avoid the cookie-cutter responses, find your win themes and weave them in, share the detail they need to make an informed decision. I haven't got a crystal ball, so I can't tell you if/when the pendulum will swing back the other way, from a buyer behaviour perspective. What I can tell you with a high degree of certainty is that prospective customers have raised the bar, in terms of their expectations from their vendor partners. It's our job now to to elevate the preparation, patience and professionalism of B2B sellers everywhere, to meet these changing needs and maintain our relevance to the customers we serve.

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

Buyers rarely choose the objectively best option. They choose the one they recognize. In many B2B decisions, familiarity plays a greater role than features or pricing. Teams may evaluate multiple vendors, but preference often leans toward the one they have consistently seen, heard, and understood over time. The reason is simple. Recognition signals safety. When a brand shows up repeatedly with clear, consistent messaging, it reduces perceived risk. Buyers feel more confident choosing what already feels familiar, even if alternatives may appear stronger on paper. This is where many marketing strategies lose effectiveness. In the pursuit of novelty, teams constantly change angles, campaigns, and positioning. But without consistency, recognition never compounds. Messaging resets instead of reinforcing, and trust takes longer to build. Repetition, when done well, is not redundancy. It is reinforcement. Each consistent touchpoint strengthens recall. Each repeated idea builds confidence. Over time, familiarity becomes preference, especially in longer B2B buying cycles. This week’s newsletter explores the psychology behind recognition, why repetition drives trust, and how to build consistency without losing relevance. For teams focused on sustainable growth, this is a shift worth understanding.

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!

95% of tech buyers aren't actively shopping right now. But... 82% will switch vendors if you catch them during their "silent research" phase. I've been testing this for 7 months with my clients at PipeBagger. Here's what actually works: 1) Dark social listening (tracking mentions of pain points across private channels). 2) Intent data mapping (identifying research patterns before RFPs). 3) Authority content seeding (being exactly where they look). 4) Hyper-contextual outreach (messaging that matches their exact research phase). The results? 3x faster deal cycles. 🚀 Why this matters: Your ideal customers are researching solutions RIGHT NOW. They're just not telling anyone. Not even their team. Here's what you need to do: - Set up social listening tools across the digital channels. - Track competitor mention patterns. - Create content that answers their silent questions. - Build authority before they need you. Because when they're ready... They'll already trust you. I'm curious: Are you already tracking your prospects' "stealth mode" research? 

How to make Out of Home that actually works New research! After 2 years researching #OOH with System1 and JCDecaux, we've combined creative measurement data with in-market brand lift and sales lift studies for the very first time. We've created the seven creative effectiveness principles of posters. And unlike most OOH creative guidance, these are truly evidence-based. They link creative choice to the branded emotional response from consumers and then to brand and business impact in the market. I've done a podcast with Mi3Australia, the force of nature Paul McIntyre, Scott Jenkins and Cristina Smart sharing a first look at all the insights. Linked that below but will be sharing more on here over the coming weeks, including decks and white papers. Honestly, one of the key insights is that marketers overestimate how much active attention outdoor advertising gets. But we saw the more brand assets a poster is loaded with ... the less short-term effectiveness! The key is choosing the right assets and using them correctly in the ad. Beyond that, we've demonstrated that creative choices can DOUBLE an out-of-home commercial lift (more store visits, sales conversion, etc). And taken shown that posters that put on a show with entertaining creative features attract more attention and create more emotion - lifting long-term effects. I love what we do, marrying creative and media choices back together. This is an excellent example of the value the System1 and JCDecaux partnership delivers for the industry. Playbook coming soon but let me know what you think of the podcast! I share #advertising and #marketing research daily, follow for more.

Here’s the hidden pipeline killer most sales teams ignore. ~43% of deals aren’t lost to competitors. They weren't even lost to "no decision." They were lost to competing initiatives. While you're focused on beating your direct competitors, the real battle is for budget and attention against entirely different priorities. Your prospect has 25 projects competing for limited resources. Only 5-7 will get funded. Is yours one of them? Most sales teams are completely blind to this reality. They track competitive wins and losses but ignore the bigger threat. Here's how innovative sellers are addressing this hidden pipeline killer: 1️⃣ Map the priority landscape They ask directly: "What are the top 3-5 initiatives your team has committed to this quarter?" If your solution isn't aligned with one of these, you're already losing. 2️⃣ Identify the zero-sum game For every "yes" to your solution, something else gets a "no." The best reps ask: "What would have to come off your plate to make room for this project?" 3️⃣ Quantify the cost of inaction When initiatives compete, ROI isn't enough. You need to establish the cost of NOT implementing your solution. "What happens if this problem continues for another year?" 4️⃣ Connect to strategic priorities Tactical projects get cut first. Strategic initiatives survive. Top performers always tie their solution to the company's publicized strategic goals. 5️⃣ Prepare for budget reallocation Innovative reps build relationships with the teams who control resource allocation. "Who else is competing for the same resources? How are those decisions made?" Your competition isn't just other vendors. It's everything else your buyer could spend time and money on instead.