Digital Sales Expert Stories
Conor Moynagh
Head of VC @ HubSpot For Startups
Dublin, Ireland
Most salespeople are great at presenting solutions, but the elite performers are masters at asking the right questions. ​ In today's digital landscape, buyers are >70% through their journey before they even talk to sales. Your job isn't to educate them on features - it's to uncover the strategic implications they haven't considered. ​ This applies to all markets and all segments. The reps who consistently hit President's Club don’t necessarily have to be the best presenters; they’re the ones who can connect the dots between a prospect's current challenges and future opportunities. They never speak to potential customers with a mentality of “I’m here to sell”, and instead approach with a “how may I help you succeed” mindset.
Conor Moynagh is the Head of VC @ HubSpot For Startups and has the important role of creating & leading HubSpot's Go-to-Market Partnership Program with top VCs. His job involves the design and implementation of a structured playbook for VC/Startup collaboration as well as being a Mentor and Coach to Startups. A key goal of his is to drive strategic engagement and scale best practices globally while expanding HubSpot's market share in the UKI Startup Sector. Conor also works on the HubSpot EMEA Product Council which focuses on establishing streamlined, efficient, and innovative systems & operations that support organisational effectiveness for HubSpot Sales teams.
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1. Leading HubSpot's GTM Partnership Program with top VCs is a significant undertaking. What was the most crucial element you focused on when designing and implementing a structured playbook for VC/Startup collaboration?
The first crucial element, which will be familiar to all GTM experts, was ICP feedback - getting out there, speaking with VCs, discussing ideas and proposals, running experiments.
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In strategic partnerships, everything is written in pencil, particularly in the early stages and even more so given the rate at which things change in today's landscape. Playbooks can’t be too prescriptive. They should present frameworks that have flexibility.
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I run with a ‘hypothesis approach’ to things. There is no wrong answer:
- If something works - great.
- If it doesn’t work - that doesn’t mean it was wrong or we failed, it still helps us figure out the next move and just means that initiative won’t be part of it.
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Creating feedback loops and mutual value architecture is crucial for programs like this to be successful!
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2. You’ve helped scale startups and coached VCs. What’s one common mistake you see founders repeatedly make in their go-to-market strategy?
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They fall in love with their product instead of solving their customers' problem.
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I see this constantly - founders who can pitch their product features for hours but can't articulate their customers' pain point in 30 seconds. They've built something technically brilliant but forgot to validate it with the market.
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They say "our product is for everyone" or "we're the Uber for X." That's not a GTM strategy; that's a recipe for burning cash. The most successful founders I work with obsess over one specific customer segment first, nail that playbook, then expand.
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An easy-to-apply litmus test for founders:
- If you can't explain why someone would buy your product at 12 AM after three pints, your messaging isn't clear enough.
- And if you can't identify your ideal customer's biggest frustration without mentioning your product, you're building in the wrong direction.
3. Having led both direct and channel sales teams, in your opinion, what’s one underrated skill every high-performing digital sales professional should master today?
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Strategic curiosity.
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Most salespeople are great at presenting solutions, but the elite performers are masters at asking the right questions.
​
In today's digital landscape, buyers are >70% through their journey before they even talk to sales. Your job isn't to educate them on features - it's to uncover the strategic implications they haven't considered.
​
This applies to all markets and all segments. The reps who consistently hit President's Club don’t necessarily have to be the best presenters; they’re the ones who can connect the dots between a prospect's current challenges and future opportunities. They never speak to potential customers with a mentality of “I’m here to sell”, and instead approach with a “how may I help you succeed” mindset.
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This skill becomes even more critical in channel sales, where you're not just selling to end customers but enabling partners to sell effectively. You need to understand their business model, their customer base, and their competitive landscape. Strategic curiosity turns you from a vendor into a strategic advisor.
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4. You've lived and worked in places like New Zealand and Latin America, how have those global experiences shaped your approach to working in the tech landscape?
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Living in New Zealand taught me that proximity doesn't equal opportunity - some of the most innovative companies I worked with were solving global problems from the bottom of the world. That experience shaped my belief that great ideas can come from anywhere, and successful GTM strategies must be locally relevant while globally scalable.
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Different markets have dependencies on different GTM channels. We, in Europe, largely see WhatsApp as a personal-use medium. Latin America sees it as one of the biggest revenue channels for small businesses. Brazil, for example, was a pioneer market for WhatsApp Pay, allowing users to make payments to small businesses directly through the app using various cards.
In fact, Brazil, Mexico, Peru, and Colombia are the top 4 countries recording the highest WhatsApp business revenue.
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5. HubSpot for Startups is growing rapidly, how do you personally spot a startup with high growth potential?
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A lot of it comes down to the founder/s. Successful startups are led by founders who strike a balance between conviction and adaptability.
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I reference a framework I’ve termed The Labrador/Bull graph, which helps identify whether a founder is building not just a product, but a learning machine. The highest-growth startups almost always come from teams who combine audacity with agility—big bets that are constantly tested and refined.
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6. What's the most common "aha!" moment you see in the startups you mentor, particularly in relation to their digital sales strategy?
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"We need to sell to the person who has the pain, not the person who has the budget."
Your ICP may not write the check!
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Most startups default to selling to whoever they think can sign the check - usually a C-level executive. And yes, they should be in the conversation, particularly as the details progress through the sales cycle - but the magic happens when they realize the actual user (who feels the pain every day) is often their strongest advocate and can influence the decision-maker more effectively than any sales pitch.
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I see this breakthrough constantly. A founder will say, "We've been pitching to MDs, but they struggle to see the value in our LegalTech tool." Once they start building relationships with the end users first, their close rates skyrocket because they're solving real problems, not theoretical ones. A champion of your product at your prospective client is the best marketing & sales resource combined.
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This insight completely changes their content strategy, their demo approach, and their customer success methodology. They stop creating content for executives and start creating content for practitioners. They stop doing high-level demos and start showing actual workflows. It's a complete GTM transformation that usually happens in a single conversation.
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7. What do you think the future of the online sales industry looks like + which AI and tech trends (and skills) should digital sales professionals be preparing for over the next 2–3 years?
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The future belongs to AI-augmented relationship builders. It will be a Human-First, AI-Powered, and Hyper-Personal landscape.
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Over the next 2–3 years, I believe we’ll see the convergence of three powerful forces: AI-driven automation, deep personalization, and a return to human-first selling—but at scale.
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AI will handle the tactical stuff - lead scoring, email sequencing, basic research - but human salespeople will focus on strategic relationship building and complex problem-solving. Think of it as moving from "hunter" to "architect" - you're designing solutions for complex business challenges, not just closing deals.
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Three skills to master now:
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Prompt engineering for sales - AI Co-Pilots Will Become Table Stakes. So learning to extract insights from AI tools to personalize outreach and identify opportunities. Understand what AI can, and can’t, do.
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Data fluency and Cross-functional collaboration - As sales cycles become more complex, sales pros need to interpret data, not drown in it. And will need to orchestrate multiple stakeholders (product, customer success, marketing) seamlessly.
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Empathy and Strategic storytelling - AI can handle more repetitive tasks and can generate content, but let your human layer be your differentiator: Build trust, be curious, and craft narratives that connect emotionally with specific audiences.
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We can’t compete with AI on speed. AI can’t compete with us on insight or context.
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8. Do you recommend any useful digital sales tools or platforms that can help professionals raise their online sales expertise?
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In today’s online sales landscape, success is driven by intelligent systems, not just individual effort. The best sales pros build their edge by combining process, tech, and personal mastery.
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Unsurprisingly, HubSpot Sales Hub remains my top recommendation - not just because I work here, but because I see the data. Our free CRM gives teams pipeline visibility and automation capabilities that would have cost thousands just five years ago. The AI-powered features like predictive lead scoring and automated sequences are genuine game-changers. And because HubSpot encompasses more than just Sales, it helps you become a more rounded seller by understanding the full customer lifecycle.
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Beyond that:
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Conversation intelligence or a Call Recording tool (like Gong)
- These tools use AI to analyze calls and surface.
- Talk ratios, objection trends, and deal risks, and can run comparisons to what the top performers globally are doing.
- Most importantly, it enables you to be present on calls, actively listen, and have a live conversation - rather than writing notes and missing the “between the lines” context.
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LinkedIn
- Sales Navigator is still unmatched when it comes to account mapping, warm introductions, and trigger-based prospecting.
- Your professional network can be your sales superpower. As buyers expect to self-educate these days, the modern sales funnel looks more like a web of peer influence, product experience, and content signals. Sales pros need to build presence and brand. They need ecosystem intelligence—knowing who’s connected to who, where conversations are happening, and how to show up with value.
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Knowing how to use AI Co-Pilots or Sales Agents correctly
- Like I mentioned in the last question, prompt engineering is a skill worth investing time in.
The best investment isn't in tools; it's in yourself, and in understanding your customers better than anyone else in your space. Tools are just accelerators.