SALES LEADERS! This 1 thing is killing your revenue (and here's how I fixed it for 50+ companies)

I’ve spent years working inside and alongside growing B2B companies, and the one pattern that continues to reveal itself is this: revenue breaks wherever the customer lifecycle breaks.

For all the talk about sales enablement, marketing alignment and AI transformation, most organisations are still operating with disconnected tools, disjointed processes, and fragmented data. And if there’s one thing I’ve learned helping teams modernise their HubSpot ecosystem, it’s that none of the exciting stuff, automation, AI, personalisation, forecasting, works unless your foundations are aligned.

In this article I want to break down the principles, lessons and practical insights I’ve picked up while helping companies, from lenders to manufacturers to recruiters, connect their systems, fix their data, and build tech stacks that actually support the way their teams work.

Why I built Heyoo (to fix the lifecycle problem)

I founded Heyoo for one simple reason: businesses rarely have true ownership of their full customer lifecycle.

Most agencies and consultancies focus on a single function, sales, marketing or service. But customer journeys aren’t linear, and every function relies on the one before it doing the right things with the right data.

When a marketing team is manually sending event permission letters one-by-one…
When a sales team is generating NDAs and proposals through three different tools…
When a service team is using DocuSign while the sales team uses PandaDoc…
When operations can’t trust the data because nobody is capturing it consistently…

…it becomes impossible for any company to scale.

The lifecycle only works when every team, every tool and every data point are connected. That belief shaped the DNA of Heyoo. It’s also why we’ve evolved from a marketing agency into a consultancy that focuses on true lifecycle system integration.

The foundation of everything: "Blueprint Before Build"

When companies ask us, “What’s the first thing you configure when setting up HubSpot?”, the truth is… it’s not in HubSpot.

The first step is blueprint planning:

• What does your lifecycle actually look like?
• What data do you collect at each stage?
• Where does that data come from?
• How does it evolve as the customer moves between teams?
• Which systems need to feed HubSpot, and which need HubSpot to feed them?

Without this clarity, teams end up buying tools, creating objects, building workflows and configuring pipelines based on personal preference, not operational reality.

A recent example: a commercial lending company whose entire application process involved JotForm → a manual rewrite into HubSpot → manual creation of agreements in PandaDoc. They were spending nearly £3k a year on tools, and even worse, creating errors that damaged client trust.

Blueprinting revealed the real issue: data was being duplicated, re-entered and overwritten at multiple stages, turning simple tasks into business risks. From there, automation and integrations become easy, and massively valuable.

Why Iintegrations are the heart of modern CRM

Most companies are now realising that to truly benefit from AI and automation, they need clean, connected systems. And the most exciting work we’re doing right now is custom integrations, particularly with ERP, accounting, loan-management and applicant-tracking systems.

Here’s a recurring pattern across clients:

• They generate mission-critical intelligence in external systems (e.g., loan portals, ATS platforms, ERP workflows).
• That data is “gold dust” but trapped.
• Teams manually rewrite, re-enter or duplicate information to get it into HubSpot.
• Errors multiply, and insights get lost.

When we integrate those systems into HubSpot, suddenly:

• Sales sees real-time operational data.
• Service knows what’s been promised and what’s been delivered.
• Leadership trusts forecasts and capacity plans.
• AI has clean, contextual data to work with.

This is where companies experience their biggest transformations, not because of “AI”, but because the infrastructure finally supports intelligence.

Where most teams struggle (Quote-to-Cash)

If I had to pick the most painfully manual part of the lifecycle for most businesses, it's quote-to-cash.

For many companies, it still looks like:

• sales building quotes manually
• operations building orders manually
• finance validating them manually
• manufacturing or service teams receiving incomplete information

Errors creep in, handoffs stall, morale drops, and the customer experience suffers.

Native quoting tools are improving, but there’s still a long way to go, especially when companies need CPQ-level complexity or true document automation inside HubSpot. This is where integrating specialised tools or automated document systems becomes critical.

The best advice I can give: clear definitions + embedded guidance

One of the biggest breakthroughs in our own methodology has been rethinking how we handle lifecycle, lead stages and deal stages.

We used to let clients lead the conversation. Now we lead with structure.

Using tools like Supered, we embed:

• stage definitions
• required properties
• data expectations
• coaching guidance
• “what good looks like” examples

The result?

Sales reps stop improvising their pipelines.
Data quality stabilises.
Handoffs improve.
Leadership trusts the reports they’re seeing.

It may not sound glamorous, but clarity scales.

Essential tools for a modern HubsSpot sales stack

When I look at the highest-performing teams, I consistently see a blend of:

• ‍Data Enrichment. HubSpot credits, Apollo and similar tools set the foundation for all downstream work.‍
• Intent Visibility. Tools like Warmly or Breeze Intelligence help reps prioritise prospects based on real buying signals.‍
• Activity Layer Apps. Surfe & HubLead for LinkedIn and Aircall for calling pull the full picture into HubSpot.‍
• Document Automation. NDAs, access agreements, proposals and contracts must move quickly and consistently, this is non-negotiable. And Portant is the ONLY tool we recommend for this‍
• (Emerging) Deal Room Software. Still early days for us, but the potential is huge.

Most teams don’t need dozens of apps, they need the right small set of tools implemented properly and tied into a clear lifecycle.

What I’d fix in HubSpot if i were rebuilding it

If I could rebuild the sales stack from scratch, my top priorities would be:

1. ‍Rethinking the Lead Object It behaves differently from deals, syncs ownership rules unpredictably, and creates friction between pre-sales qualification and pipeline management.‍
2. Native Document Automation Documents should be treated like properties, structured, version-controlled, reportable and easy to organise across the lifecycle. Which, coincidentally, Portant has completely solved. It's so seamless now that it feels like a native HubSpot feature.‍
3. Better Goals & Forecasting Teams need flexible goals (ARR, NRR, lead targets) and accurate progress calculations. Right now, it’s too rigid and too hard to report on.

These aren’t “nice-to-haves”. They’re core to enabling performance, visibility and alignment across the revenue engine.

The future: A shift to true "Go-to-Customer" alignment

The biggest trend I’m watching isn’t a new AI model or tool. It’s a shift in how companies think about go-to-market.

For years the conversation was: “Let’s align sales and marketing.”
Then it became: “Let’s align the front office.”

Now it’s becoming: “Every team that touches the customer must operate as one system.”

This requires big cultural change:

• Sales can’t work in the shadows anymore.
• Service teams can’t operate in isolation.
• Data accuracy becomes everyone’s responsibility.
• Leadership must enforce connected processes, not departmental preferences.

The companies who embrace this will use AI more effectively, make better strategic decisions and deliver more consistent customer experiences. The ones who don’t will struggle, not because of technology, but because of misalignment.

Final thought

Every organisation is in a different place on their digital and AI journey. But the principles remain the same: connected systems, clean data, well-designed processes, and lifecycle-wide thinking.

If you’re building a modern revenue engine, one that actually supports your people and scales with your business, you have to own the entire lifecycle, not just the slice you feel most comfortable with.

Want support building a high-performing, fully connected HubSpot ecosystem?

Check out Heyoo on the Portant Partner page and let’s explore how we can help. 👉 https://www.portant.co/partners

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