OnePortfolio

Enterprise customers often need to purchase and manage dozens — or even hundreds — of HubSpot accounts. But HubSpot's commercial systems were built around managing one account at a time.

I led design for a multi-account experience that streamlined sales setup and quote approvals, brought individual quotes into a more cohesive customer purchasing experience, and established a path toward centralized portfolio management.

The challenge wasn't simply to improve individual workflows. It was to coordinate an experience across multiple systems and teams without requiring a foundational rebuild — and to preserve the broader customer opportunity when organizational priorities shifted.

In HubSpot, a portal is an individual account: a separate workspace with its own data, users, and billing.

For smaller businesses, this model works well. Larger organizations often need multiple portals: a franchise might need one per location, a holding company might maintain separate accounts for regional businesses, and a brand network might manage distinct business units.

But HubSpot's buying experience was built around a one-to-one relationship between an account and its commercial records:

As the number of accounts grew, so did the complexity. A customer purchasing 50 portals could face 50 separate quotes, contracts, invoices, and renewal timelines — even when the purchase involved the same products and commercial terms.

The friction across the lifecycle

The friction extended beyond operational inefficiency. It undermined HubSpot's enterprise proposition at the moment customers were deciding whether to buy.

"One of the reasons my point of contact has said over and over that HubSpot is not an enterprise solution."— HubSpot Customer Success Manager, describing the difficulty of purchasing and managing multiple portals

Why it mattered to the business

The opportunity was concentrated among high-value, upmarket customers. Approximately 8,500 existing customers were identified as qualifying for the experience, with a projected $50M+ incremental ARR opportunity associated with a 5% improvement in upmarket win rate.

This was an opportunity estimate, not realized revenue. Addressing it required more than making an individual screen faster: we needed to rethink the buying experience across multiple systems, teams, and stages of the customer relationship.

I organized the problem around three milestones across the customer lifecycle. Each addressed a different part of the same underlying issue: customers and internal teams needed to coordinate multiple accounts as one relationship, even when HubSpot's systems still treated them individually.

A multi-account sale required reps to repeat the same sequence for every portal:

Reps often switched between deals just to check approval status, while building spreadsheets reportedly consumed around 20% of the relevant team's week. The tools were organized around individual portals and quotes, but reps needed to manage the overall opportunity.

As a product team, we explored a new object: the portfolio — a group of portals purchased and managed together by one organization.

I designed a portfolio-based workflow that gave sales reps one place to coordinate the opportunity, from account and deal creation to quote configuration and approval tracking. The portfolio supported different commercial terms across accounts, while allowing reps to reuse quote configurations when multiple accounts shared the same products and pricing structure.

The workflow enabled reps to:

1. 01Create a portfolio for the customer.
2. 02Create multiple portals in bulk.
3. 03Create deals for those portals in bulk.
4. 04Configure and submit quotes for the relevant deals.
5. 05Copy a configured quote across multiple deals when accounts shared the same products and pricing.
6. 06Track deal progress and quote approvals from the portfolio view.

Design decision 1: Make progress visible in one place

I used HubSpot's Trellis table component to bring related portal and deal records into a single portfolio view. I introduced an approval-status column so reps could see which quotes were approved, pending, or still in draft.

This made the portfolio a practical workspace for coordinating the overall opportunity — not simply another place to view account data. It also addressed the need for external spreadsheets by giving reps a centralized view of progress.

Design decision 2: Extend an existing capability to reduce repetitive work

Quote copying already existed at the individual-deal level. I had originally designed that capability as part of the Rep Quoting Experience team. For Multi-Account Management, I extended it to work across multiple deals in a portfolio.

This allowed reps to reuse a configured quote rather than repeat the same setup for every account when products and pricing aligned. When commercial terms differed, each deal could still retain its own quote configuration.

The principle was to make repeated work easier without forcing accounts into identical terms.

Design decision 3: Coordinate the opportunity without collapsing individual records

The portfolio connected the work across accounts and deals, while each quote remained associated with its individual deal.

This distinction mattered: we could improve the end-to-end workflow without requiring a fundamental change to the underlying commercial model.

Even after reps prepared the quotes, customers still faced separate purchase and signing flows for each portal. Deal Desk sometimes completed checkout on customers' behalf, adding manual effort to an already fragmented process.

Work within the existing architecture

An ideal direction would have been a single multi-account deal containing subscriptions for each portal. However, the existing subscription and revenue-recognition architecture was built around individual accounts and quotes. Making that larger change wasn't feasible within the delivery timeline.

The team instead pursued a Combined Order Package: bringing individual quotes together into one customer-facing document while preserving the underlying quotes and deals. This enabled a single DocuSign signing experience, subject to legal and billing requirements.

Design challenge: Make portfolio-wide validation actionable

For a Combined Order Package to be valid, every quote had to meet specific requirements:

• Use invoice payment terms.
• Have matching net payment terms.
• Use DocuSign as the contract-signing method.
• Be valid and unexpired.
• Share the same expiration date.

Ideally, these settings would be managed at the portfolio level. But the system still treated each portal and quote individually, so reps needed to ensure every quote was configured correctly before creating a package.

My first approach was inline validation. I explored identifying mismatched terms directly in the workflow so reps could understand what needed to be corrected without running a separate validation process.

After reviewing the approach with Engineering, we learned that inline validation wasn't feasible within the delivery timeline. The team needed to validate the entire portfolio in a single action.

I adapted the design in partnership with Engineering. The next iteration introduced a validation modal with a checklist that ran the required checks across the portfolio. It identified individual quotes that needed attention and flagged mismatched terms, giving reps a consolidated view of what was preventing package creation.

The trade-off was moving away from more immediate, inline feedback in favor of a single portfolio-wide validation step. While less seamless, the checklist made the validation process transparent and actionable while meeting implementation constraints.

Design challenge: Make a long purchase easier to understand

Combining individual quotes into one package simplified signing, but introduced a different problem: the resulting document could be long and cumbersome to review. Customers could sign once, yet still struggle to understand the full purchase.

To address this, I partnered with an SDII on the Quote Buying Experience team to ideate a Combined Order Package Summary Page — an at-a-glance overview that brought the most important information together upfront.

The summary concept included:

• Total amount due at signing.
• Total value of the package.
• Account-level details to help reviewers understand what they were purchasing.

The intent was to help customers scan a complex package without having to piece together the details or calculate totals themselves.

The challenges didn't end at purchase. People responsible for many accounts still lacked a consolidated view of renewals, invoices, and billing details. I explored a broader portfolio-management vision centered on consolidated visibility, proactive oversight, and centralized updates.

Find a feasible first step

When organizational priorities shifted, portfolio management was deprioritized. I brought the problem to the Director of Product, who connected me with the Account & Billing team.

With that team's Q4 capacity already committed, I proposed a smaller initial scope: a read-only Portfolio Dashboard that would give customers visibility across their accounts while allowing them to navigate to an individual portal to take action.

The proposed first release included:

• A consolidated list of portals.
• Upcoming renewals.
• Pending invoices.
• Navigation into individual portals to manage account-level tasks.

More advanced capabilities — such as editing billing details centrally, managing centralized versus distributed payment arrangements, and making bulk billing updates — would remain outside the initial scope.

Outcome: Keep the customer problem on the roadmap

The Account & Billing team adopted portfolio management onto its Q4 roadmap, creating a path for continued work on the post-purchase experience.

By reframing the opportunity around a smaller, read-only dashboard, I helped preserve the underlying customer problem and connect it with the team best positioned to address it.

The dashboard was roadmap work, not a shipped outcome. Its proposed scope created a potential first step toward centralized portfolio visibility and future billing capabilities.

Progress across the buying lifecycle

The project addressed the multi-account challenge across internal sales setup and customer purchasing, while establishing a path toward post-purchase management.

• Sales workflow efficiencyThe portfolio-based workflow replaced repetitive account-by-account setup with bulk creation, quote copying, and centralized approval tracking. The reported comparison was a reduction from a process that could take two weeks to one completed in minutes. The underlying evidence and measured pilot impact should be confirmed before presenting this as a validated result.
• A more cohesive purchase experienceThe Combined Order Package brought individual account quotes together into one customer-facing document, enabling a single signing experience instead of separate signing flows for every portal. The summary page concept explored how to make the resulting package easier to scan and understand.
• Business opportunityThe initiative targeted approximately 8,500 qualifying high-value customers and a projected $50M+ incremental ARR opportunity associated with a 5% improvement in upmarket win rate. This was the estimated opportunity the work aimed to address — not revenue directly generated by the design.
• A path toward portfolio managementAlthough the broader portfolio-management vision was deprioritized, the Account & Billing team adopted the work onto its Q4 roadmap. This preserved a potential path toward centralized portfolio visibility and future billing capabilities.

This project reinforced that enterprise design is often about reconciling three things: the experience customers need, the systems the business has today, and what the organization can realistically deliver.

Starting with the object relationships helped establish a shared model before we moved into screens. Engaging Engineering early surfaced a foundational constraint before we invested further in an ideal solution the existing system couldn't support within the available timeline.

I also learned that a successful design outcome doesn't always mean delivering the entire vision. When priorities shifted, narrowing the scope of portfolio management created a practical path forward while preserving an important part of the customer value.

The work I find most meaningful goes beyond simplifying complex workflows. It's helping teams align on the problem, make informed trade-offs, and find a way forward when the ideal solution isn't immediately possible.

Looking back

If I were continuing this work, I'd validate the end-to-end experience with customers managing large portfolios and measure its operational impact across the lifecycle — not just how quickly reps can set up accounts, but how much manual work the purchase process eliminates and whether centralized billing visibility reduces ongoing customer friction.

I'd also partner with the Account & Billing team to define success measures for the proposed read-only dashboard before implementation. That would help the team assess whether the initial release delivers meaningful value and use those insights to prioritize the next set of billing capabilities.

Ultimately, this project reinforced that designing at scale requires both systems thinking and organizational influence. The best path forward isn't always a complete technical rewrite or a fully realized end state. Sometimes it's finding the right layer of experience to deliver meaningful value today while creating a foundation for what's next.