Principal, Sales AI Strategy & Execution

The Principal, Sales AI Strategy and Execution is a senior individual contributor on Tipalti’s Data team and supporting the Sales organization. Sitting at the intersection of AI strategy and Sales revenue execution, this role is a key driver of Tipalti’s AI-led growth transformation - the person who continuously transforms the AI-powered tools and workflows that enable our Sales Development, Sales, Solutions Consulting, Account Management, and Alliances teams to deliver a world-class buying and selling experience at every stage of the customer journey.

You close the gap between what a world-class data and AI team can build and the associated workflows for optimized execution and results. You bring enough technical depth to configure intelligently, and enough Sales domain expertise to translate field needs into precise requirements without losing anything in translation. You collaborate closely with Tipalti’s data and AI teams cross-functionally, while maintaining the ability to drive the AI-led growth roadmap forward independently. You own the roadmap, build the timelines, and measure and own the outcomes.

You will operate core elements of Tipalti’s AI-powered Sales tech stack, whether that means orchestrating and configuring new capabilities, designing workflows across the customer journey, or extending existing platforms to unlock new value for the field. You will bring our AI use case roadmap to life in collaboration with our AI teams alongside our Sales Excellence team and in collaboration with key stakeholders across the Sales organization, and over time, a foundational force in Tipalti’s AI-led growth transformation.

Why Join Tipalti?

Tipalti is the AI-powered platform for finance automation, elevating how finance teams operate in the global economy. We empower our customers to scale faster and smarter by removing the complexities of doing global business and accelerating their finance operations efficiency.

Our platform provides a comprehensive suite of finance automation solutions designed for mid-market businesses across accounts payable, global payouts, procurement, employee expenses, corporate cards, supplier management, tax compliance, and treasury.

At Tipalti, we pride ourselves on our collaborative culture, the quality of our product, and the capabilities of our people. Tipaltians are passionate about the work they do and keen to get the job done. Our culture ensures everyone checks their egos at the door and stands ready to reach for success together.

In This Role, You’ll Be Responsible For:

Tipalti’s AI-augmented sales ambition is not a collection of standalone features. It is a unified system that works across teams, workflows, and stages of the buying and selling journey to create a seamless, world-class experience for both the buyer and the seller. Your objective is to architect and optimize the system and execute on this vision for accelerated scalable growth that is both effective and efficient

• Manage  AI-powered Sales tools and related processes, whether built internally, configured from third-party platforms, or delivered in partnership with our data and AI teams, and be accountable for their ongoing performance, evolution, and measurable field impact

• Approach our Sales organization with a systems mindset, designing for interoperability across the full Sales stack, breaking down workflow silos, and ensuring data, context, memory, and intelligence flow seamlessly across the buying and selling journey rather than accumulating in disconnected tools

• Coordinate the build and continuously evolve our capabilities for Sales teams

• Develop deep platform proficiency and configure the workflows, agents, automations, and integrations that translate AI capabilities into daily jobs-to-be-done for AEs, SDRs, SCs, AMs, and Alliance Managers

• Regularly test and deploy workflow automations, tool integrations, and AI-powered processes, API connections, and native capabilities across the Sales stack. Including Salesforce, Clari, Clari Copilot, ZoomInfo, Actively, Hyperbound, Openprise, HockeyStack, Gainsight, 6Sense, Outreach, and Sumble

• Evaluate emerging tools and capabilities with a complete customer life cycle mindset — configuring proof-of-concepts, validating with the field, and scaling what works — while maintaining documentation that keeps the system coherent and maintainable as it grows

Bridge the Field and Drive the Roadmap

You are equally at home talking to an AE about why a workflow isn’t hitting right and talking to a data engineer about API schema design. You surface what the field needs, translate it into what gets built, and own the roadmap sequences

• Work directly with AEs, SDRs, SCs, AMs, and Alliance Managers to surface workflow friction, unmet needs, and AI use case opportunities, translating field insights into precise technical requirements and prioritized roadmap decisions

• Operate as the Sales org’s internal voice for AI tools, owning the use case intake process, backlog prioritization, and delivery accountability across teams’ motions

• Collaborate closely with Tipalti’s data and AI teams on shared use case design, data quality requirements, and architectural decisions, serving as the primary voice of the Sales field in cross-functional AI discussions while maintaining the ability to configure and deploy independently on Sales-specific use cases and systems

• Coordinate cross-functionally with Sales Ops, Enablement, Marketing, Operations, Customer Success, Finance, and Alliance stakeholders to ensure use cases align to the broader revenue motion and don’t create friction at journey handoff points

• Represent the AI-led growth roadmap to Sales leadership — translating technical progress into field impact and pipeline implications, and maintaining a transparent view of what is shipping, what is delayed, and why

Measure, Iterate, and Report

• Define success metrics for every tool, workflow, and AI capability deployed — before build and report on the related output metrics

• Analyze performance data, AI output quality, and field adoption signals to continuously improve outcomes across the buying and selling journey

• Deliver regular reporting to Sales leadership on AI tool performance, workflow adoption, and revenue impact across all supported Sales motions

About You

• 10+ years of experience in a Sales organization, with at least 4+ years of experience in a technical, systems, hybrid Sales/builder role. You understand how the field works because you’ve been close to it, and you know how to build systems, workflows, and use cases that the field actually uses

• Proven technical proficiency: API fluency (reading documentation, configuring integrations, configuring webhooks, troubleshooting data flows), and hands-on experience deploying AI-powered Sales systems in production (i.e., not just proof-of-concepts)

• Experience owning AI-powered tools or products in production. You know what it means to be accountable for a live system’s performance, iterate on it continuously, and hold it to a measurable standard

• Deep understanding of Sales Development, Sales, Solutions Consulting, Account Management, and Alliances motions, including prospecting, pipeline management, deal execution, partner-sourced pipeline, and expansion workflows

• Proficiency across the modern Sales stack: Salesforce, Clari, Clari Copilot, ZoomInfo, Actively, Hyperbound, Openprise, HockeyStack, Snowflake, Gainsight, Outreach, and Sumble; and hands-on experience with AI and automation platforms including Claude, Gemini, Workato iPaaS, Gumloop, n8n, Zapier, Make, or equivalent

• Strong communicator who operates fluently across technical and non-technical stakeholders with the ability to prioritize and sequence a technical roadmap under real-world constraints, and represent complex work clearly to senior leadership

• Experience in B2B SaaS or a complex, multi-product Sales environment is highly preferred

• Highly self-directed with a bias toward action: you identify what needs to change before you're asked, and you own the outcome.

Base Salary Range: $135,000 - $165,000 CAD annually.

The compensation information, above, reflects our reasonable expectation for this role based on several factors, including current market conditions. Final compensation will be determined through individual assessment of experience, skills, qualifications, and other job-relevant factors. Actual offers may vary within or, only in exceptional circumstances, outside the stated range based on the candidate's unique qualifications and our comprehensive evaluation process. We are committed to equitable compensation practices in compliance with applicable employment laws.