Procurify: Product Strategy & Operations Lead

Know Your Interviewer: Jonathan Su

Background

• CPTO at Procurify since Sep 2025 (6 months in — still building his team and operating rhythm)
• Previously SVP Product & Engineering, Spend Management at U.S. Bank (4 yrs) — led integration of Bento for Business after acquisition, launched AI-powered Spend Management product
• Before that: CTO at Bento for Business (5 yrs) — fintech for SMBs, expense cards, B2B payments. First engineering hire, built from scratch through acquisition
• Co-founder/CTO of LeadLedger (acquired by ZoomInfo)
• Founding Engineer at Cloudwords (acquired by Welocalize)
• Earlier: Cisco, Citi, IBM
• Education: Cornell MS Computer Science, UC Irvine BS CS

What He Values (from recommendations + posts)

• Quality and customer obsession — "his passion for delivering a highly quality product and experience to customers is second to none"
• Technical depth AND design/UX sense — "cared just as much about UI/UX details as he did ensuring scalable infrastructure"
• Team culture — "always open to providing and receiving feedback," "respectful for everyone's opinion and point of view"
• Execution speed — "deliver overnight what others would discuss the architecture of for weeks"
• Ambitious builders — his hiring post: "roles with real ownership and impact, and a close partnership with me and the team"

Why He Joined Procurify

• "I felt the pull to build something bold and meaningful"
• Vision: AI not just for automation but for intelligence — "empowers finance and procurement teams to gain control, predict outcomes, and move with confidence"
• He's been in spend management/fintech for 9+ years (Bento + U.S. Bank + now Procurify)

What He's Probably Looking For In You

• He's 6 months in — likely still establishing his operating rhythm. He needs someone who can build that foundation with him, not just maintain it
• Deep technical background means he'll respect technical fluency — don't shy away from architecture details
• He's been a founder/CTO — he values people who take ownership and move fast
• His career pattern: small company → acquisition → integration at large co. He understands platform migration, org scaling, and navigating complexity after M&A — your Ting story will resonate

Know the Company Context

• Procurify: AI-powered procurement, AP, expense, and payment platform for mid-market orgs
• CEO Chad Gaydos joined Jan 2025 (ex-SAP 18 yrs, Skillsoft COO, Talkdesk COO) — GTM and operational excellence background
• Both CEO and CPTO are new — the company is in transformation/scaling mode
• Remote-first, Canada-based, venture-backed
• AI push is central: "Pulse 2025" summit featured Microsoft partnership (Zia Mansoor, CVP Cloud & AI)
• Chad's recent post: "AI isn't 'coming' to spend management in 2026. It's already separating the leaders from everyone else."
• CARES values: Commitment Ambition Resilience Excellence Simplicity

"Tell Me About Yourself" / "Walk Me Through Your Background"

Frame your arc around the role: strategy → operations → bridging technical and business → scaling through complexity

• Autzu (2 yrs): Startup, drive-sharing for Uber drivers in Toronto. Operations Manager → Senior Product Ops Manager. Worked directly with CEO and COO/Founder, attended investor meetings, bridged customer support + software dev + leadership. Tracked utilization KPIs, managed fleet operations at a scrappy scale.
• Ting Internet / Tucows (4 yrs): Fiber ISP, subsidiary of Tucows. Progressed from service design PM → digital experience PM → Senior Manager, Solutions Operations (IS team). Led website redesign + brand transition, built self-scheduling system, then owned the full platform migration — 50K customers across 5 billing systems. Reported to and bridged two CCOs across Ting and vendor (WaveLow). Built and managed a team of 2 direct reports.
• Through-line for Procurify: "Across both roles, I've been the person who connects strategy to execution, bridges technical and business teams, and brings clarity to complex, cross-functional programs — which is exactly what this role is."

"Tell Me About a Complex, Cross-Functional Program You Led"

Lead with the migration story — it's your strongest for this role

The Migration (Ting, 2023–2024)

• 50,000 customers across multiple legacy systems, complicated by 3 acquisitions and 5 different billing systems
• Not a 1:1 migration — multi-step, from a legacy monolith + fragmented CRMs/billing systems into a new platform built by vendor (WaveLow)
• I scoped the entire project: high-level data mapping, phasing strategy, identified all data sources and structures
• Had access to and understood all legacy systems — I was the connecting node between tribal knowledge holders at Ting and WaveLow's technical teams
• Original deadline was end of 2023 for the full migration — I pushed back, showed execs what was realistic, set expectations on what we could deliver
• Delivered Phase 1: 30,000 customers (from the monolith) in ~3–6 months, before year-end — a major milestone
• Phase 2 was harder: remaining 20K across fragmented systems, including enterprise customers with unstructured data and different schemas
• Before mat leave (April 2024), defined scope/goals/obstacles for remaining phases, split work across 2 direct reports, and shifted accountability to WaveLow for technically-heavy execution

The Vendor Relationship Complexity

• WaveLow spun out of Ting/Tucows in ~2021, taking the entire engineering org and most technical product people
• Ting was left with zero software developers — no technical execution capacity
• No clear vendor agreement initially — expectations were assumed, not documented
• WaveLow had scoped their responsibility narrowly (just migration scripts) but lacked visibility into Ting's customer data
• I surfaced the expectation gaps to both CCOs, pushed for more vendor access to Ting systems AND more technical enablement for Ting teams
• Regular 1:1s with WaveLow's CCO to represent Ting's needs and expectations clearly

JD Mapping

• Strategic Planning Scoped project, defined phasing, pushed back on unrealistic timelines
• Exec Communication Presented status to two CCOs, synthesized technical complexity for business audiences
• Cross-Functional Bridged vendor tech team, internal ops, business experts, and C-suite
• Accountability Made invisible expectations visible, drove clarity on vendor vs. internal responsibilities
• Risk Visibility Identified that full migration by EOY was unrealistic before anyone else flagged it

"How Do You Handle a Crisis?" / "Tell Me About Something That Went Wrong"

The billing silent failure story

Billing Silent Failure (Ting, ~Sep 2023)

• After new platform went live, new customers were being billed through a Kafka event-driven orchestration (order system → billing component → Stripe)
• A misconfigured/missing event meant payments never reached Stripe — failed silently for 4+ weeks
• AR team caught it during month-end close — major revenue discrepancy from prior month
• Impact: hundreds of customers, ~$100/month avg = tens of thousands in missed revenue
• Billing was on rolling dates (per subscriber activation date), so couldn't batch-fix — had to triage daily
• What I did: Immediately escalated to skip-level CCO, brought in CFO + CTO. Coordinated triage across engineering, accounting, customer support, and Stripe account manager
• Core fix within ~1 week to resume payment processing
• Customer support had to call customers to explain missed charges — managed that operational coordination too

JD Mapping

• Risk Visibility System had zero observability on a revenue-critical flow — I traced and surfaced it
• Cross-Functional Triage Finance, engineering, CS, external vendor (Stripe) — all in days
• Escalation Judgment Knew when to pull in CFO/CTO vs. handle internally
• Commitment (CARES) Owned the outcome, didn't pass the buck

"How Do You Bridge Technical and Business Teams?"

You can pull from multiple stories here

Ting: WaveLow Vendor Relationship

• WaveLow had technical capability but no customer data knowledge; Ting had domain expertise but no engineering
• I was the single point translating between both sides for two CCOs
• Surfaced actual capabilities and access limitations to execs on both sides — not just "we need help" but specific gaps and what it would take to close them

Ting: Enabling Self-Service for GTM Teams

• After frontend was rebuilt (monolith → Webflow + JS framework), I spent ~1 year training marketing and sales teams to self-serve on the website
• Gave them Webflow access control: campaigns, A/B testing, content changes — without waiting on engineering (which no longer existed at Ting)
• Reduced a hard technical dependency to a self-service workflow

Ting: Address Serviceability Fix

• Identified that the backend address check was using a Google Maps radius hack with no real source data
• Brought in GIS team to build discrete address database
• "It wasn't officially my job, but it was the right thing to do" — influence without authority

Autzu: CEO/Founder Partnership

• Before Chief of Staff was hired, worked directly with CEO on operations and with COO/Founder on running the business
• Attended investor meetings alongside CEO and COO
• Connected customer support, software dev team, and executive leadership

"How Do You Drive Accountability and Operating Cadence?"

Migration Project Tracking

• Built the scoping, data mapping, and phasing artifacts for the migration from scratch — nothing existed before me
• Presented project status, resources, and timelines to both CCOs regularly
• Created documentation for operational teams during parallel-system transition (massive change management)
• Before mat leave: documented scope, timelines, and obstacles so clearly that work could be divided across 2 direct reports and the vendor

Go-to-Market Rollout

• Phased the website/platform launch by market (smaller, more structured markets first, then expand)
• Managed the transition period of running parallel systems with extensive documentation
• Coordinated change management across all operational teams

Autzu: Utilization Tracking

• Tracked weekly utilization hours (6 four-hour blocks per car per day) as the core business KPI
• Connected operational data to business decisions at a startup with tight resources

"Why This Role?" / "Why Procurify?"

Tailor based on what resonates most with you — some angles to consider:

• The role matches my actual career pattern: I've consistently been the person who connects strategy to execution and bridges technical + business teams — at Autzu with the CEO/COO, at Ting across multiple C-level execs and a vendor. This role names that as the job, not a side responsibility.
• Transformation moment: New CEO, new CPTO, AI push — Procurify is building its next operating model. I've done this before (Ting's platform migration was exactly this kind of "new era" transition).
• Spend management is a real problem: Having worked with 5 billing systems and seen what operational chaos looks like when financial data is fragmented, I understand the pain Procurify's customers face.
• Jonathan's profile resonates: Technical founder who scaled through acquisition — similar to the Ting/WaveLow/Tucows dynamic I navigated. I'd be working with someone who gets the complexity.

"What Questions Do You Have For Me?"

Prioritize questions that show strategic thinking and genuine curiosity about the org

About the Role & His Needs

• You're about 6 months in at Procurify — what does the current operating rhythm look like for R&D, and what's working vs. what needs to change?
• What's the biggest gap this role fills for you day-to-day? Where do you feel most stretched right now?
• How do you envision the working relationship between us? What does "trusted advisor" look like in practice to you?

About the Org & Strategy

• With both a new CEO and CPTO, what's the biggest strategic shift the R&D org is going through right now?
• How mature are the current planning and execution processes? Am I building from scratch or evolving what exists?
• What does the relationship between R&D and GTM look like today? Where are the friction points?

About AI & Product Direction

• Chad's been vocal about AI being the differentiator in procurement. How is the R&D org structured to deliver on that vision?
• What's the balance right now between platform modernization and new AI capabilities?

About Success

• What would success look like in the first 90 days for this role?
• What's one thing that, if this person gets it right, would make the biggest difference for you and the team?

Quick Reference: Key Numbers

• Migration: 50K total customers, 30K in Phase 1, 3–6 months, 5 billing systems, 3 acquisitions
• Billing issue: 4+ weeks silent failure, hundreds of customers, tens of thousands in missed revenue, ~1 week to core fix
• Website: Launched late spring/early summer 2023, phased by market, still live at ting.com
• Scheduling: 35%+ SMS response rate, reduced outbound call volume
• Team: Grew from 1 to 2 direct reports at Ting (Senior Manager, Solutions Operations)
• Autzu: Fleet of cars + ~10 accessibility vans, 4-hour rental blocks, Uber partnership

Reminders

• Frame for the audience Jonathan is deeply technical (CS from Cornell, founding engineer, CTO). Don't oversimplify — he'll appreciate architecture details (Kafka, Stripe integration, monolith breakup, data schemas).
• He's hiring his partner This isn't a "prove you can execute" interview. It's "can I trust this person to be my force multiplier?" Show judgment, not just delivery.
• He's 6 months in He's still building. Show that you can help build an operating model, not just run one that already exists.
• CARES: Simplicity "Focus, clarity, and streamlining to cut through complexity" — when telling stories, emphasize how you simplified, not just how complex things were.
• Dish/Mobile detail Keep out of main migration story. Use only if probed on why data was complex.