Sr. Manager, Sales Tooling & AI

Groupon•Chicago, IL

1d•Hybrid

About The Position

Groupon is a marketplace where customers discover new experiences and services everyday and local businesses thrive. To date we have worked with over a million merchant partners worldwide, connecting over 16 million customers with deals across various categories. In a world often dominated by e-commerce giants, we stand out as one of the few platforms uniquely committed to helping local businesses succeed on a performance basis. Groupon is on a radical journey to transform our business with relentless pursuit of results. Even with thousands of employees spread across multiple continents, we still maintain a culture that inspires innovation, rewards risk-taking and celebrates success. The impact here can be immediate due to our scale and the speed of our transformation. We're a "best of both worlds" kind of company. We're big enough to have the resources and scale, but small enough that a single person has a surprising amount of autonomy and can make a meaningful impact. Role Purpose: The Sr. Manager of Sales Tooling & AI is a strategic and technical leader responsible for architecting, optimizing, and scaling Groupon’s sales technology ecosystem, with primary ownership of Salesforce and Salesloft. This role sits at the intersection of Sales, Sales Operations, Engineering, and Analytics, ensuring our sellers are equipped with intuitive, automated, and AI-enabled tools that drive productivity and performance. This leader will modernize and simplify a historically layered sales tech stack by establishing a clear point of view on systems architecture, automation strategy, and AI-forward solutioning. The mandate is not simply to administer tools, but to transform them into a competitive advantage by reducing friction, improving data integrity, and enabling intelligent workflows that drive measurable commercial outcomes. The Sr. Manager will lead a high-performing team of Salesforce Administrators and Business Program Managers responsible for CRM governance, sales engagement optimization, automation, integrations, and continuous innovation across the sales technology landscape.

Requirements

8–12+ years of experience in Sales Operations, Revenue Operations, Sales Technology, Engineering, or related roles in mid-to-large enterprise environments.
5+ years of deep, hands-on Salesforce experience, including architecture, automation (Flows), integrations, and data governance. Salesforce Admin and/or Advanced Admin certification strongly preferred.
Strong expertise in Salesloft (or comparable sales engagement platform) with demonstrated success driving adoption and measurable productivity gains.
Proven experience designing and implementing automation strategies that improve sales efficiency.
Exposure to AI-enabled sales tools, predictive modeling, or workflow intelligence solutions.
Experience leading and developing technical or systems-focused teams.
Strong stakeholder management skills in matrixed, cross-functional environments.
Highly analytical, systems-oriented thinker with the ability to connect tooling decisions to commercial outcomes.

Responsibilities

Sales Technology Strategy & Architecture
Define and own the strategic roadmap for Salesforce, Salesloft, and the broader sales tech ecosystem.
Establish scalable architecture standards, governance models, and integration frameworks.
Partner with Sales Leadership and Sales Ops to translate business priorities into system capabilities and workflow design.
Rationalize legacy tools and technical debt to simplify the seller experience.
Salesforce Ownership & Optimization
Serve as the executive owner of Salesforce strategy, configuration, data model integrity, and user experience in conjunction with the Engineering department.
Lead enhancements across pipeline management, forecasting, account hierarchy, territory alignment, and reporting.
Drive automation of manual workflows and process improvements.
Ensure data governance standards and scalable object architecture that supports evolving business models.
Salesloft & Sales Engagement Excellence
Own the strategy, implementation, and optimization of Salesloft.
Design structured cadence frameworks aligned to funnel strategy and segmentation.
Improve seller adoption through workflow integration with Salesforce and enablement best practices.
Leverage Salesloft analytics to continuously refine outreach effectiveness and pipeline generation.
Automation & AI Forward Solutioning
Identify and implement automation opportunities that eliminate low-value administrative work for sellers.
Partner with Data & Analytics to embed AI-driven insights into daily sales workflows (e.g., next-best-action, prioritization, lead scoring).
Evaluate and pilot emerging AI tools that improve seller productivity, forecasting accuracy, and engagement quality.
Ensure AI initiatives are practical, measurable, and integrated into core operating processes.
Reporting, Insights & Performance Enablement
Collaborate with Analytics to define the core sales data model and system-driven metrics.
Enable real-time visibility into pipeline health, activity effectiveness, and productivity drivers.
Ensure tools reinforce desired sales behaviors and align with incentive design and performance frameworks.
Change Management & Adoption
Lead change management for new tools, automations, and system enhancements.
Drive high adoption through structured communication, training, and feedback loops.
Establish clear SLAs, intake processes, and prioritization frameworks for system requests.
Team Leadership & Cross-Functional Partnership
Build and develop a high-performing Sales Tooling team, including Salesforce administrators, system analysts, and automation specialists.
Act as a trusted partner to Sales Leadership, Marketing, Engineering, Finance, and Data teams.
Balance speed and innovation with governance, compliance, and long-term scalability.