Tom B.

Sr. Director, Finance Operations & AI Automation | $1B+ Billings Org | Building the AI-Native Finance Function at Tenable

Washington DC-Baltimore Area

About

Senior Director of Finance Operations and AI Automation with a decade-long track record of scaling billing operations at Tenable from $150M to over $1 billion in total billings without adding net new headcount. I lead global Billing Operations and Order Management while serving as the company's internal AI and automation leader for Finance, personally building and deploying production-grade tools that eliminate manual work, reduce cost, and create capacity for the team to focus on higher-value work. I sit at the intersection of finance operations, systems architecture, and AI-native tooling. I build what others spec out, move faster than traditional development cycles, and translate complex operational problems into solutions that leadership can see and measure. Outside of Tenable, I am a member of the Bowe Fellowship, a competitive leadership development program for emerging executives in the Baltimore/Washington region, and a recipient of the Tenable Leadership Excellence Award.

Experience

  • Tenable (10 yrs)
    • Senior Director, Finance Operations & AI Automation
      May 2026 - Present · 3 mos

      Over the past decade, I've scaled billing operations from ~$150M to over $1B in total billings with zero net new headcount by making automation a core operating principle. Today I lead a cross-functional AI mandate across Finance, building multi-agent workflows, AI Skills, automation, and real-time analytics that free my team to focus on higher-value work.

    • Senior Director, Global Billing Operations
      May 2025 - May 2026 · 1 yr 1 mo

      Claim to fame: Scaled Tenable's Billing Operations past $1 billion in total billings while holding headcount flat and successfully merging the Order Management and Billing teams into a single, unified, global function of 10. - Built the Credit & Collections Hub internally, replacing a $250K+ vendor solution and recovering 8 to 12 hours of weekly capacity for the collections team - Engineered the EOQ Tracker Suitelet in NetSuite, giving leadership a real-time view of invoicing and early renewals at quarter close, enabling CCB forecast accuracy within 50 basis points of actuals - Redesigned the SOX Undelivered Emails process, cutting daily review time from 60 minutes to 10 minutes and converting a daily compliance control into a monthly one - Appointed Factory Leader for Tenable's Finance AI initiative, driving automation across billing, forecasting, and order processing to reclaim significant annual capacity across the entire Finance organization - Delivered three (3) production-grade automation tools in a single fiscal year using AI-assisted prototyping, compressing timelines that previously required full development cycles - Supported Tenable's growth past $1 billion in total billings while holding headcount flat, scaling entirely through process redesign and automation - Expanded into LATAM with a dedicated business partner model, achieving parity with EMEA and APJ frameworks and reducing order friction ahead of deal close - Upleveled the entire Billing Operations team effective May 2026 by redesigning roles to reflect technical, SOX-relevant, automation-driven work - Selected for the WTCI Bowe Fellowship for emerging executives in the Baltimore/Washington region for next generation executives - Recognized with the Tenable Leadership Excellence Award and presented at a co-CEO roundtable

    • Director, Global Billing Operations
      Mar 2023 - Apr 2025 · 2 yrs 2 mos

      Claim to Fame: Revolutionized the Billing Operations team by introducing new automations, resulting in cutting order processing time by 50% and automating 98% of standard orders, while significantly enhancing global regional presence and scaling the team to support over $1 billion in total billings. - Launched a self-service Distributor PO Portal integrated with the company’s order management and billing systems, reducing manual order touchpoints by 50% and accelerating quote-to-cash cycles in a high-volume SaaS environment. - Automated 98% of standard orders for provisioning/invoice purposes streamlining the revenue recognition process - Successfully expanded the global presence by onboarding two new Billing Operations Managers in Singapore and the United Kingdom, enhancing regional capabilities and support, growing the teams regional presence by 50%. - Collaborated with Sales Operations and Partner Operations to eliminate duplicative processes, driving operational efficiencies in the Order to Cash process and streamlining workflows across departments resulting in 35% of receipt of the Purchase Orders to be automated. - Mentored and promoted team members, elevating a Billing Analyst to Senior Billing Analyst and a Billing Operations Manager to Senior Manager, Billing Operations, contributing to the team’s ability to scale beyond $1 billion in total billings. - Streamlined team processes by eliminating redundant tasks and developing team skills to remove single points of failure, ensuring more efficient and reliable operations across all functions of the team. - Developed and implemented key financial reports using Tableau, reducing manual reporting efforts by 4 hours per report and improving accuracy. - Provided a clear vision and strategic direction for the team, fostering a culture of continuous improvement and operational excellence that supports the company’s growth objectives.

  • Wegmans Food Markets (9 yrs 5 mos)
    • Cafe Manager
      Mar 2016 - Jul 2016 · 5 mos

      -Analyze financial reports and product trends, and react with the aim of increasing profitability in the departments -Demonstrate team building by communicating a common purpose, empowering team members to contribute their best and selecting candidates with a variety of skills and styles for inclusion on the team -Practice process improvement daily by implementing positive change and continuously look for ways to improve processes and combine tasks into an effective workflow by maximizing resources and ensuring high standards and quality is achieved -Advise others within the organization and external business partners using relevant knowledge and skills to ensure that sound business decisions are made

    • Manager, Program Management - Sales & Demos
      Jun 2013 - Jul 2016 · 3 yrs 2 mos

      Claim to Fame: Successfully implemented a sales training process and sales teams at 7 stores across Maryland resulting in sales increase of 269% in targeted sales items over a 6-month period - Increased the Maryland Divisional Sales by 269% after implementing a Demo Program with dedicated team members and trainings within 6 months - Created weekly sales reports utilizing a data warehouse to present weekly sales numbers to regional and executive teams - Trained over 300 employees and leaders across the division best practices for educating customers about Wegmans Brand Products - Planned and Executed regional store events to bring more customers to our stores such as the annual Hatch Chile event, Farmers Market event, and Menu Magazine events - Implemented new sales programs, Seafood and Meat Cooking Classes, teaching over 50 customers how to cook various seafood and meat products - Held weekly stakeholder meetings with Executive leaders across the Maryland Division to report on progress, impediments, and improvements - Created a program playbook to teach leaders in other stores how to be successful with their Sales Teams in different environments and markets - Collaborated and planned events at each store with our Wegmans Brand Ambassador thus increasing awareness of Wegmans Brand products

    • Customer Service Desk
      Oct 2011 - Jun 2013 · 1 yr 9 mos

      - Provide Incredible Customer Service - Provide customer solutions - Data Entry - Understand complex computer systems

  • Front Desk Agent at Marriott Hotels
    Apr 2014 - Jun 2016 · 2 yrs 3 mos

    - Process all guest check-ins by confirming reservations, assigning room, and issuing and activating room key - Process all payment types such as room charges, cash, checks, debit, or credit - Process all check-outs including resolving any late and disputed charges - Answer, record, and process all guest calls, messages, requests, questions, or concerns - Coordinate with Housekeeping to track readiness of rooms for check-in - Communicate parking procedures to guests/visitors - Supply guests with directions and information regarding property and local areas of interest - Run daily reports (number of arrivals, departures), identify any special requests, and check reports for accuracy - Complete designated cashier and closing reports in the computer system - Cash guests' personal checks and traveler's checks - Count bank at the beginning and end of shift - Balance and drop receipts according to Accounting specifications. - Maintain records pertinent to the guests staying in the hotel - Responsible for the proper functioning of all phases of Front Desk operation and to perpetuate high standards of quality and areas of important

  • Night Auditor at Homewood Suites by Hilton Hotel
    Feb 2013 - May 2013 · 4 mos

    -Assumes managerial responsibility when General Manager is absent from worksite -Check in/Check out guests -Operate sophisticated POS & hotel software (OnQ)

  • Attractions Host at Spaceship Earth at Walt Disney World
    Jan 2010 - Jun 2010 · 6 mos

    -Monitor guest flow and provide a safe guest experience