Strategies to Increase Enterprise Software Sales

As CEO of Cognism, it's my goal to have our first salesperson earn over $1M this year. Here are the 5 key steps we're taking to achieve this (and why $1M/year sellers is a critical enterprise metric): 1. Refine ICP and Increase Enterprise Pipeline Focus Throwing enterprise sales reps to the wolves to “figure it out” is the default and wrong. Force feeding them accounts based on what’s working downmarket is also wrong. You can’t sell big deals without selling to the right customers and it's not up to the ENTs to figure it out. That’s why we're dropping ALL of our assumptions and doing an organisation-wide deep dive of our current ICP, customer base and acquisition strategy. Our incredible new CRO Rob Tomchick will then ensure pipe is built in markets and segments that generate the highest revenue, ACV and win rates. 2. Adjust Comp Structure and Incentivize Risk Many companies *unintentionally* incentivize short term deals by putting the wrong comp structure in place. That’s why we’re redesigning ours to be attractive enough to push reps to NOT SETTLE for just a small small slice of the ENT pie. This is terrifying for some leaders, but you have to incentivize sellers to take risks. They need the upside if you want them to push your product into more regions and departments, which lengthens the sales cycle and increase the number of DMs. 3. Give Sellers More Support and Selling Time No one closes multi-million dollar deals alone. You need a committed deal team available to your sellers 24/7. In addition to sales engineers, you need full exec, presales and product support throughout the sales cycle. We're also giving our sellers access to our new GenAI tools which will enable them to spend more time hunting. Thoughtful, creative and strategic enterprise selling dies with unnecessary data entry. 4. Differentiate Enterprise Product Positioning Echoing point #1, assuming your *current* product and positioning will work up market is a mistake. We got a head start on GenAI and are backtesting with live Enterprise customers to ensure our sellers hit the market with premium and differentiated offerings. 5. Renew Focus on Training and Enablement You can’t expect bigger results from your team with “check the box” training. Our most promising initiative is the adoption of MEDDICC. We’re already seeing success from our reps and managers utilising it to monitor deal health. Our enablement efforts have also expanded 5x to include individual mentoring and coaching. Why do I think $1M/year reps is an important metric? Because it ensures you're thinking about building product for your customers that can deliver that level of enterprise value and building the most efficient sales process to achieve it. Salespeople communicate the value of your product to the market. And companies that undervalue their salespeople grow slower. That's why for us, $1M/year isn’t just a number. It’s a symbol of excellence, dedication, and the potential of our team.

Most sellers only uncover ONE level of impact in discovery. That’s why their deals stall, why their ROI slides don’t land, and why their champions can’t sell internally. The truth? There are 4 levels of impact—and if you miss even one, you’re selling half-blind. Selling is helping. But helping means going deeper than “company KPIs.” Here’s the framework I coach every AE on when they’re trying to win enterprise SaaS deals: 1. Company Impact This is where 90% of reps stop. “What’s the cost savings? What’s the revenue upside?” That’s table stakes. If you don’t tie your software to actual numbers—lost revenue, margin impact, labor cost—your ROI story collapses in front of a CFO. Example: A Service Cloud rep I coached quantified millions lost in unbooked hospital referrals because of missed scheduling calls. That turned a “$500K tool is too expensive” into “8X ROI, no-brainer.” 2. Buyer Impact Your champion has skin in the game. They left a stable job. Their reputation, career trajectory, even their family’s well-being are tied to this project. If you can show them how your solution makes them the hero internally, you create unstoppable personal buy-in. 3. User Impact These are the people who log in every day. If they hate the tool, adoption dies. If they love it, productivity soars, morale improves, turnover drops. Shadow them. Ask what frustrates them. Show them a better day in the life. 4. Customer Impact The most overlooked layer. How does your product improve the end customer experience? Faster service, better outcomes, less stress? For a hospital, it’s not about “efficiency.” It’s about a patient getting a life-saving scan booked in hours instead of days. Stop selling features. Stop selling “savings.” Start selling IMPACT. - Company. - Buyer. - User. - Customer. Miss one—and you’ll miss the deal. Hit all four—and you’ll never sell the same way again. Selling is helping. Always.

"We've been working this deal for 8 months and it just went dark." (Ouch!) Last week, I had three different sales leaders tell me versions of this same story. Big enterprise deals that seemed "sure things" suddenly stalling or disappearing completely. Here's what's really happening: You're selling like it's 2015, but buyers have fundamentally changed how they make decisions. Seriously, the old playbook is dead: → Build relationship with one champion → Demo your product extensively → Negotiate on price to close → Wait for their "decision timeline" Why this fails in modern enterprise selling? #1 Committee-based buying Average enterprise deal now involves 6-8 decision makers. Your single champion can't drive consensus alone, no matter how much they love your solution. #2 Risk-averse buyers Post-2008, post-COVID, buyers are terrified of making bad decisions. They'd rather stick with status quo than risk their careers on your "game-changing" solution. #3 Budget complexity Money exists, but it's trapped across departments. Your champion in IT loves you, but the budget owner in Finance has different priorities. Here’s how elite enterprise sellers win these days: A. Multi-thread from Day One Map the entire buying committee before you pitch anything. Identify the economic buyer, technical evaluator, user champions, and potential blockers. Build relationships with each. B. Sell business outcomes, not features Stop talking about what your product does. Start quantifying the business impact of not solving their problem. Make the cost of inaction higher than the risk of action. C. De-risk the decision Provide case studies from similar companies. Offer pilot programs. Create implementation roadmaps. Give them ammunition to defend the decision internally. D. Control the process Don't ask "What's your timeline?" Tell them "Based on your goals, here's the optimal implementation schedule." You drive urgency, they don't. Here’s a real life example: One client was stuck on a $400K deal for 6 months. We mapped 8 stakeholders they'd never engaged. Built business cases for each department. Deal closed in 45 days at $650K. The difference? They stopped selling a product and started orchestrating a business transformation. Enterprise deals aren't won in demo rooms. They're won in boardrooms, budget meetings, and implementation planning sessions. Sales leaders, how are you implementing this across ALL your reps? Want to talk about how we could help? Go here: https://lnkd.in/ghh8VCaf

In 6 years, I was promoted 3 times to become the youngest L7 Sales Leader at AWS, leading a team that hit 119% attainment on >$150M yearly quota. Here are 5 hard lessons I learned about enterprise sales: 1. Enterprise Sales = Team sport Winning big deals means selling internally as much as externally. I spent almost as much time getting internal resources, securing executive buy-in, and aligning product teams as I did in front of the customer. 2. Trust Beats Price Every Time I’ve seen won deals where we weren't the cheapest option. Why? Trust. Building relationships where the client believes in your long-term partnership is the single biggest lever you can pull in enterprise sales. 3. FOFU > FOMO The buyer doesn’t care about FOMO as much as they care about FOFU: fear of fucking up.The biggest question they’re asking themselves is, “Will this decision get me fired?” Your job is to make the deal as risk-free as possible. 4. Always Build a Business Case Enterprise buyers need justification for spending big. If you’re not building a clear, data-backed business case, you’re asking your champion to sell for you—and they won’t. The stronger the ROI/COI (cost of inaction) argument, the easier the sale. 5. You’re Not the Hero, You’re the Guide Perhaps the most important thing to internalize. Your role shifts from salesperson to strategist. EMPOWER. Don't OVERPOWER. Guide your champion on how to sell internally. Set a clear, step-by-step strategy with them. Orchestrate the entire process—internally and externally—and ensure all the pieces are aligned and moving in the same direction. TAKEAWAY: In enterprise sales, you’re the quarterback. not the one carrying the ball to the endzone. Your job is to: orchestrate the play, guide your champions, and set your team up for success. It's not about doing it all yourself; But leading the right people in the right direction at the right time.

Last week I spoke with Salesloft CEO David Obrand about the massive 40,000 seat deal they closed with IBM. Here are the 3 critical elements of their enterprise sales playbook: 1. Non-tech GTM orchestration and product marketing Ensure that you have coordinated revenue motions for each industry vertical you are targeting. Historically, the big VC-backed sales and marketing tech companies have grown on the backs of selling into tech itself.  But the future of sales and marketing tech sits within the true enterprise and most of the true enterprise is decidedly not tech.  To enter the healthcare, financial services, industrials, or government services markets you’ll need dedicated sales teams, services teams and account-based marketing motions that make it clear to the buyer you deeply understand their problems and their issues.  It’s not going to come from super bowl ads.  2. Leverage ecosystems Going it alone into the enterprise can be a daunting task. To effectively drive enterprise adoption, you’ll need support and assistance from partners and ecosystem players in the space.  IBM isn’t just a Salesloft customer, they’re also a partner, helping introduce the concept of revenue orchestration to thousands of their customers.  If you don’t have relationships with the big IT consulting arms of the major strategy firms (eg Deloitte), make sure you begin to develop them. They are critical trusted entry points into the enterprise. Being on the AWS app exchange isn't enough. You need deep partnerships that give confidence to enterprise buyers you are a bet worth making and that there is infrastructure capable of supporting you.  3. Invest in Customer Success and introduce them pre-sale Introducing a new workflow product to a company with 40,000 employees isn’t a “set it and forget it”. Getting 40,000 people to do anything, let alone use your new product, is hard.  Whether you call it strategic account management, customer success, or something else doesn’t matter. What matters is that you are focused and have a plan for driving usage and adoption and that the plan begins before the sale happens. Investing in CS pre-sale also helps drive GTM alignment and makes sure that the sales team is selling something the services team can stand behind. TAKEAWAY: The enterprise will decide who wins the B2B SaaS wars. Few companies actually have experience building deep and lasting relationships within the enterprise.  If you want to do it, you’ll need a playbook. This is a great place to start.

You can easily add $20k/month to your B2B SaaS heading into 2025. Here’s how: Target High-Intent Keywords Most SaaS companies target broad, high-competition terms like “CRM software”. These don’t convert. You're wasting your time. What to do instead: Focus on long-tail keywords tied to purchase intent. Examples: “Sales automation software for SaaS onboarding” “Enterprise CRM with HubSpot integrations” “HIPAA-compliant marketing platform for healthcare” Map keywords to the buyer journey: Use cases, verticals, and technical needs. Use tools like SEO Stuff to find: KD <30 Volume: 100–1,000 searches/month High CPC: A sign of strong intent. Vertical-Specific Pages Create dedicated landing pages for each vertical, use case, and target audience. What works: Specific Industries: /crm-for-manufacturing, /sales-automation-healthcare Page Components: Industry compliance Integration capabilities Social proof: Case studies, logos, testimonials ROI metrics: Show tangible value for the vertical. Link these pages together with a content hub to boost topical authority. Long-Form Content B2B SaaS buyers need in-depth content to make decisions. Write 2,000+ word resources that align with enterprise buying cycles. Content Ideas: “Enterprise CRM Implementation Guide: Timeline, Costs, ROI.” “How Healthcare Teams Achieve HIPAA Compliance in Marketing Automation.” “ROI Analysis: Sales Automation Tools for SaaS Companies.” Structure to Follow: Executive Summary (key findings for decision-makers) Technical Requirements (integrations, deployment specs) ROI Benchmarks and Case Studies Actionable Next Steps with clear CTAs. Schema Markup Add FAQ, Product, and Review schema to boost search visibility. Comparison Pages Own the comparison phase of the buying journey. What to create: “HubSpot vs [Your Tool]: Enterprise Integrations and Security.” “Top Alternatives to Salesforce for Manufacturing Teams.” Key Page Elements: Features: Side-by-side comparisons. Compliance: Security, HIPAA, SOC 2. Customer Case Studies: Show why others switched to you. Content Clusters Build resource hubs to dominate topics relevant to enterprise buyers. Example Hub and Cluster: Hub: “Enterprise CRM Implementation.” Cluster Pages: “Enterprise Security Standards for CRMs.” “How to Plan Enterprise Data Migration.” “Training Programs for CRM Adoption.” “Measuring ROI for CRM Deployments.” Internal linking between these pages boosts topical authority and visibility. Video Content Use demos, security breakdowns, and implementation guides to engage users and increase dwell time. Retargeting Ads Keep enterprise leads engaged with whitepapers, ROI calculators, and case studies. 90-Day Plan: Days 1–30: Research keywords, create vertical pages, implement schema. Days 31–60: Publish guides, launch comparison content, and thought leadership. Days 61–90: Build clusters, add videos, and run retargeting ads.

Most B2B teams suck at marketing to technical IT buyers. Here is why: They try to replicate what works to sell to economical buyers: Linkedin Ads → personalized outreach → semi-custom landing pages paired with content. But what if your buyers aren't on LinkedIn? What if they ignore every cold email? What if they give exactly zero f*ck about your "streamlined solutions"? We generated multiple enterprise deals with senior IT buyers, and I can say for sure - these audiences are notoriously skeptical of "traditional" marketing. Here is what works based on our case studies: Testrail: https://lnkd.in/dgmAxcuf Postindustria: https://lnkd.in/dKMiy-DN Glorium Tech: https://lnkd.in/dwJ6APG9 1. STOP SELLING. START PROVING. Technical buyers don't respond to "here is your challenge - here is our solution" message . They research on their own, read documentation, and test products before talking to anyone. Before launching any ABM program to IT buyers: - Make sure your product documentation is crystal clear - Offer a trial or sandbox environment - Validate your messaging with actual technical users - Ensure you have POC as a part of the sales process 2. LEVERAGE SPONTANEOUS ADVOCACY. Engineers trust their peers 100x more than your case studies. We found our customers already talking about the product in technical forums, YouTube, and niche communities. We amplified their voices instead of drowning them out with our own. Result: peer-driven recommendations that actually moved deals forward. 3. USE INTERNAL SUBJECT-MATTER EXPERTS. Your solution architects and technical leaders used to be your buyers. Put them front and center. What worked for us: - Educational webinars led by SMEs (not sales pitches) - Community roundtables addressing real technical challenges - Enabling technical experts to share lessons learned 4. FORGET LINKEDIN. GO WHERE THEY ACTUALLY ARE. Senior IT buyers might not engage on LinkedIn, but they're active somewhere. We targeted them through: → Niche communities → Direct mail with relevant, personalized research → Content collaborations with industry peers they already trust 5. INVOLVE THEM IN CONTENT CREATION. The fastest way to build credibility with technical audiences? Make them the experts. We invited target buyers to: - Contribute to market research - Participate in podcasts - Co-create educational content This gave us an excuse to reach out, built genuine relationships, and created peer-to-peer content that was 10x easier to distribute. My honest take: Most B2B teams will never run these playbooks. Too manual. Too much effort. They'll keep blasting automated outreach at technical buyers who will continue ignoring them. But that's good news for you. It means there's a massive opportunity to stand out by actually doing the work of understanding your technical buyers and engaging them on their terms—not yours.

Here's how I’m teaching SaaS sales teams to run a value-based sales cycle in 2025 tailored for finance approval (and why most deals still die) I’m working with multiple SaaS companies and sellers right now, reviewing live deals, sitting in on discovery, demos, and pricing calls. And across enterprise sellers, even very experienced ones, I keep seeing the same issue: We’re making enterprise selling way more complicated than it needs to be. So here’s a clean, practical breakdown of how I'm teaching sellers how to actually running a value-based sales cycle in this new market. Step 1: Set expectations before you sell anything Enterprise buyers want to be led. Early in the process, you need to explain: - How deals like this typically get approved - Who usually needs to be involved - What creates the highest likelihood of forward momentum - How the process will wok You can be direct: “In most of our successful deals, Finance or the CFO is aligned early. In 9 of the last 10, they had final sign-off ,so we plan for that upfront.” Some buyers push back. Most appreciate the honesty. This is one way you establish power. Step 2: Discovery is about isolating the business problem Discovery is not product education. The goal of discovery is to answer one question: What is the business problem, and what is it costing them? That means: - What’s broken today? - Where is money being lost, time being wasted, or risk being created? - What happens if this stays the same for another 12 months? If conversion improves, costs drop, or headcount is avoided: By how much? What does that translate to financially? You don’t need perfect numbers. You need directionally accurate business impact. Step 3: Quantify value before you ever demo Before a demo, you should be able to say: “If we solve this, here’s what it unlocks for the business.” - Revenue gained - Costs removed - Risk reduced If you can’t articulate that, the demo will be a feature tour or finance will kill the deal later. Step 4: Demo features through the lens of value Every feature must answer: What does this unlock for the business? Examples: “This is how you increase conversion by X%” “This is how you avoid hiring Y additional headcount” “This is how you reduce risk in this part of the process” Features without outcomes don’t sell. Step 5: Build pricing decks assuming Finance sees them Assume every deal goes to Finance. Because it does. Your pricing deck should be understandable to someone who: - Has never seen your product - Wasn’t on the calls - Only cares about risk and money That means: - Define the problem - Show how it’s solved - how the math and what it unlocks for the biz $$$ Step 6: Reconfirm value on pricing calls before asking for approval On the pricing call: - Re-anchor the business problem - Reconfirm the biz value - Make the financial impact obvious and close them on it If you want me to customize this for you or your sells team, lets talk and get into it!

The shift from seats to agents pressures SaaS margins. At the same time, the longstanding practice of getting enterprise customers to pre-commit and also prepay for functionality they may never deploy will get harder as CIOs look to free budget for their own LLM costs. To weather the storm, some SaaS companies have increased prices. This boosts revenue and margins in the short-term but can't be done repeatedly and creates even greater scrutiny over shelfware as procurement teams right-size and shift contracts to "pay as you go." To achieve sustainable growth, SaaS companies need to become hyperefficient at sales and marketing. Here are common ways to do so and who's doing it well: 1. PLG. Shopify and Atlassian exemplify efficient go-to-market based on product-led growth with free trials, low-friction upgrades and upsells. Their sales teams only need to get involved in the biggest opportunities at the largest accounts; every other step in acquisition, commercial transaction, activation, onboarding, and growth is self-service and automated. 2. Vertical SaaS. Guidewire Software and Veeva Systems are laser-focused on insurance and life sciences, respectively. Rather than casting a wide net, they spear-fish with deep domain knowledge and purpose-built solutions for that industry's specific workflows and regulatory requirements. Guidewire doesn't need to buy Super Bowl ads– their annual customer conference is the Super Bowl for property & casualty insurance executives. Nearly zero GTM effort is wasted– unsurprisingly they're the two most efficient on the list. We modeled Hearsay Systems after both these companies, and this focus allowed us to win incredible market share among Fortune 500 banks & insurers despite only raising $60M in totality. 3. Relocate operations to lower-cost regions and AI. This is private equity's favorite playbook to take costs out of companies they buy. Field sales continues to shift more to Zoom, which means you can hire AEs anywhere. Inside sales contributes a greater % of revenue as PLG motions are established. AI handles top-of-funnel leads qualification and generating marketing content and campaigns. 4. Focus on gross revenue retention. Because of high customer acquisition costs in #SaaS, leaky buckets are margin killers. Use LLMs to help customer success teams analyze product usage, segment cohorts, and identify opportunities to increase value realization. Put in guardrails to prevent sales reps from overselling an account, as doing so only creates churn in the next renewal cycle. 5. Introduce another product line. This only works if your new product has the same buyer as your existing products. Many SaaS acquisition pro formas fail to actualize for this reason, as it's not actually feasible to have the same AE sell both old and new products. Every SaaS company right now needs to double down on one or more of these levers in the AI era.

"We're disrupting the industry!” The CTO checked his watch. $4M deal dead in 5 words. The CTO's eyes glazed over. Fifth time this week. My client froze. His billion-dollar product roadmap reduced to a startup cliché. I've sat through 1,000+ enterprise sales meetings. Here's what nobody tells founders about selling to big companies: Your "innovation" is their "risk." Your "disruption" is their "danger." Your "revolution" is their "rebellion." Truth is, there are only 3 types of enterprise buyers: The Veterans (80%): - Want stability above all - Need proof, not promises - Buy from safety signals The Climbers (15%): - Chase calculated wins - Need evidence, not excitement - Buy from success stories The Visionaries (5%): - Build the future quietly - Need substance, not show - Buy from deep insight Last week, a founder pitched "groundbreaking AI" to a Fortune 500 buyer. The buyer's real thought? "Who wants to be the first penguin in the water?" After $100M+ in enterprise deals, here's the secret: Don't sell transformation. Sell risk reduction. Don't pitch revolution. Pitch results. Don't promise the future. Prove the present. Because in enterprise sales, the most dangerous word isn't "no." It's "maybe." And "maybe" is what you get when you speak Silicon Valley to Wall Street. Want to close enterprise deals? Learn to translate innovation into insurance. That's worth more than any pitch deck.