How AutomateNow Helped TIAA Move from Disconnected Spreadsheets to a Unified HubSpot Platform

The Challenge

TIAA had HubSpot. They had used it for years. But in practice, only the bids team used it consistently. The rest of the business operated in the way many organisations do when a CRM has not been properly embedded: each team working in its own way, with its own spreadsheets, with no shared view of what was happening across the business.

Think of it like a building where every department has its own set of keys to its own room, with no corridor connecting them. Work gets done, but nobody knows what is happening next door, and the person at the top has to knock on every door individually to get a picture of the whole.

What was breaking down

• Directors and commercial leads had no way to see deal progress, bids in flight, or revenue at risk without manually requesting individual Excel spreadsheets from team members and hoping they were up to date.
• HubSpot had an adoption rate of approximately 5% of the workforce that needed to be using it. The tool existed, but the business had not been set up to use it at scale.
• Upsells and contract renewals were managed verbally or informally. In some cases, agreements were reached but contracts were never sent. In others, invoicing was simply forgotten, resulting in direct loss of revenue.
• Onboarding, project delivery, and customer success had no shared home in HubSpot. There was no way to track a client relationship from initial tender through to delivery and renewal in one place.
• TIAA's workforce of full-time staff, part-timers, and consultants created significant reporting complexity. No single view existed of who was working on what, at what stage, and what commercial exposure that created.
• Leadership needed to see the bigger picture — not just what had been sold, but what was being renewed, what was at risk, and where growth was actually coming from.

"They knew HubSpot could solve it. But they did not know where to start, and they needed someone to come in and help them see the full picture before making any decisions."

Anna Drogon, Operations Manager, AutomateNow

The Solution

AutomateNow's recommendation was not to start with the configuration. It was to start with clarity. Before any HubSpot changes were made, the team proposed a structured full-day workshop at TIAA's offices, bringing together every department head, the commercial director, and management in one room to map the current state and define what good looked like.

The workshop approach

• A pre-workshop online session was held to introduce the AutomateNow team, allow all participants to share their biggest challenges in advance, and use those inputs to shape the workshop agenda.
• The full-day workshop was structured across four sessions: marketing audit and challenges, sales processes and pipeline clarity, customer success and project delivery, and systems and integrations.
• Different team members attended different sessions based on relevance. Heads of each department were present throughout. The commercial director attended the full day.
• AI tools were used during the workshop to capture notes and session content accurately, enabling AutomateNow to focus on facilitation rather than documentation.
• Two formal outputs were produced: a technical recommendations report mapping all existing systems, their gaps, and a detailed integration roadmap showing how each system should connect to HubSpot; and a process recommendations report covering how each department's workflows should be restructured within HubSpot.
• The integration roadmap covered five or more separate systems, assessing each for two-way versus one-way sync requirements, data ownership, and sequencing of implementation

What followed the workshop

The workshop was the turning point. Having seen the full picture of where TIAA was and where it needed to go, the leadership team made the decision to invest in a full HubSpot Enterprise rollout. The business moved from a handful of basic seats to 23 Enterprise seats and 17 Core seats — a commitment that would not have been made without the clarity the workshop provided.

AutomateNow was retained to implement the recommendations step by step. The work included building out Sales Hub for bids, tenders, and contract management, creating a structured pipeline for tracking upsells and renewals, and configuring CRM objects to support onboarding and project delivery alongside commercial activity.

The Results

Before the workshop, TIAA had three people actively using HubSpot. After the engagement, the business moved to 23 Enterprise seats and 17 Core seats, bringing the entire commercial workforce into a single platform for the first time.

Upsells and renewals that previously slipped through informally — sometimes agreed verbally, sometimes invoiced late or not at all — are now tracked within a structured pipeline. Contracts are triggered automatically when deals progress. The revenue that was previously at risk through manual process gaps is now captured systematically.

The commercial director can now see the state of the business without asking anyone for a spreadsheet. Every tender, every contract, every renewal, and every upsell lives in one place. That single change in visibility has altered how the leadership team makes decisions.

The technical integration roadmap produced during the workshop gave the business a clear, sequenced plan for connecting all five-plus external systems to HubSpot. That roadmap is now being executed in phases, each delivering a measurable reduction in the manual work required to keep data current across the organisation.

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The Impact

The impact of this engagement began before a single line of HubSpot configuration was written. The workshop itself changed how TIAA's leadership team understood their own business. By the end of the day, they had a shared language for their challenges, a prioritised view of what needed to change, and enough confidence in the roadmap to make a significant investment in the platform.

The most significant impact has been confidence. Before the workshop, TIAA's leadership team felt the weight of a system that was not working for them, but could not articulate exactly why or where to start fixing it. After one structured day, they had answers to both questions. That confidence translated directly into a commercial decision: a substantially larger HubSpot investment than the business had previously considered.

AutomateNow's approach throughout was to act as a strategic partner rather than a delivery vendor. The workshop was designed to make TIAA's teams feel capable and clear, not dependent. The outputs gave internal ownership of the direction while providing expert guidance on execution. That balance is what turned a one-day engagement into a long-term retained partnership.

AI Usage

AI was used during the workshop itself to record and process session notes in real time. This allowed the AutomateNow team to remain focused on facilitation and active listening rather than documentation, resulting in higher quality outputs and more accurate technical and process recommendations.

The two reports produced after the workshop — the technical integration roadmap and the process recommendations report — were built using AI-assisted analysis of the session recordings, ensuring that every concern raised by every department was captured and addressed in the final documents.

HubSpot's AI features are being incorporated into the ongoing implementation, particularly around contact enrichment and pipeline activity summaries, giving the TIAA commercial team faster access to the context they need before client interactions.

What's next

AutomateNow continues to work with TIAA on a retained basis, implementing the integration roadmap produced during the workshop. Each phase connects an additional system to HubSpot, reducing manual data handling and increasing the accuracy of commercial reporting. The goal is a fully connected platform where bid management, contract delivery, upsell tracking, and client renewals all operate within a single, trusted system.