Improving Sales and Billing Workflows
Led a platform level design initiative to monetize a previously free quoting product, and connect it to the previously unconnected areas of HubSpot where sales reps lived to increase downstream billing and payments usage. Led CPQ, Payments, and Growth work spanning payments enrollment, payment processing and migration, reporting, acquisition, and more.
2x
user engagement vs. first release
42%
of quote creations from new surfaces
#1
upgrade point across Commerce Hub
#1
lead to trial conversion across all of HubSpot
My Role
Design Lead
Team + Stakeholders
PO · 4 Developers · 3 Group Leads · 3 Vice Presidents
Problem
HubSpot was investing heavily in quoting, billing, and payments, but they were invisible where it mattered.
Quotes inside of HubSpot were being upgraded and reintroduced as a paid offering, but adoption was low. Quotes were invisible because we had targeted the admins, not the salespeople who use them every day.
The quotes, billing, and payments lifecycle was owned by the Revenue division, not the Sales division — so even though quotes were core to the sales process, they had no connection to the surfaces salespeople actually used. This had negative downstream impact for billing and payments as well.
Solution
A new user acquisition strategy and quote features integrated into sales surfaces
I audited 45 different product surfaces and features across the Sales division, aiming to build the highest impact that was technically feasible in a limited timeframe.
User acquisition had to work differently across user types, quote history, and account tiers: admin vs. regular user, whether they'd created quotes before, and paid vs. free all changed what users saw and when.
On top of that, we were tackling HubSpot's #1 CSAT issue, lack of connection across hubs, by bringing quotes to where sales users already spent their time. I worked with multiple teams across multiple areas of the product, where I introduced AI-powered guided actions, quote creation, and quoting visibility in the most visible areas of the product for sales users.
01
Know a quote’s status instantly and take action.
In Sales Hub, the Kanban page received 200K views and over 2M interactions daily, with 41% of users relying on the Kanban board to take action on deals. Quotes weren't visible there at all.
For users with quotes, statuses are surfaced instantly and let them act on the quote directly. If a quote doesn’t exist, AI suggests when to create a quote or can generate a quote draft if enough information is present.
02
Quotes are embedded into sales surfaces, not a hidden afterthought.
AI-powered guided actions trigger based on quote activity, prompting users rather than acting for them: before a quote exists, the prompt is to create one; once created but unsent, the prompt is to send it; once sent and awaiting a response, the prompt is to follow up with the client.
An activity feed gives further visibility into quote actions, surfaced in multiple places throughout HubSpot.
03
The quote to cash lifecycle is front and center.
Quotes are now surfaced natively in the Deal Record centerbar. Quote status, buyer engagement signals, and next-step prompts can be seen without leaving the deal record, and are repeated in the CRM sidebar.
AI can now auto-detect relevant deal information and suggests the next step in the quote-to-cash lifecycle.
04
Upgrade paths depend on the user's account status, quote activity, and if they were mid-workflow.
A user’s upgrade path depended on three factors: paid vs. free, active vs. inactive, and where they were in their workflow, evaluated the moment they hit "create quote" or tried to access a dedicated quotes page. "Active" was defined as a published quote within 6 months, marking high intent. Paid Sales Hub accounts legally needed access regardless of activity.
Users who were mid-workflow, such as entering from high-traffic areas like the sidebar, weren't interrupted and went straight to the legacy editor. Inactive or no-access users were routed straight to the upgrade page, while active legacy users saw an easy-to-bypass informational prompt.
Initially, leadership wanted a more aggressive approach, but user feedback led us to our initial designs that gave users more of a choice rather than a full page block.
Impact
The highest trial to upgrade conversion across HubSpot
Reverting to the original upgrade paths doubled user engagement. 42% of all quote creations came from these new surfaces. Once the paid offering was introduced, the updated quote sidebar became the most popular upgrade entry point across all HubSpot features.
2x
user engagement vs. first release
42%
of quote creations from new surfaces
#1
upgrade point across Commerce Hub
#1
lead to trial conversion across all of HubSpot