Sr. Manager, Sales Tooling & AI

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.

Key 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.

Qualifications:

• 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.

We Are Looking For:

• Systems Architect: Thinks in terms of scalable design, clean data models, and long-term sustainability.
• Product Mindset Operator: Treats Salesforce and Salesloft as evolving products, not static tools.
• Automation Champion: Obsessed with eliminating manual effort and increasing seller focus on revenue-generating activity.
• AI Pragmatist: Excited about AI innovation but disciplined in applying it where it drives measurable impact.
• Adoption Driver: Understands that a tool only matters if sellers use it effectively and consistently.

How We Measure Your Success:

First 2-3 Months

• Clear, documented sales tooling roadmap aligned to commercial priorities.
• Improved Salesforce data hygiene and workflow efficiency.
• Increased Salesloft adoption and measurable improvements in activity-to-pipeline conversion.
• Reduction in manual seller administrative time through automation initiatives.

3–6 Months

• Embedded AI-driven workflows that improve prioritization, forecasting accuracy, and outreach effectiveness.
• Streamlined tech stack with reduced redundancy and improved integration stability.
• Measurable gains in seller productivity and pipeline velocity attributable to tooling enhancements.

Longer Term

• A sales technology ecosystem that is intuitive, scalable, and AI-enabled.
• Sellers spending more time selling and less time navigating systems.
• Sales Tooling recognized as a strategic lever for revenue growth and operational excellence.

Why You'll Love Working Here:

• High-impact role with visibility to senior leadership – Help shape the systems that power Groupon’s global sales organization.
• Opportunity to influence the future of a global public company – Play a key role in modernizing the technology and workflows that drive our commercial growth.
• Entrepreneurial environment where your contributions matter – Move quickly, simplify complexity, and see your work translate into real business impact.
• A culture that values curiosity, ownership, and results – We empower people who take initiative, challenge the status quo, and deliver outcomes.

The Details:

• Location: Downtown Chicago (hybrid, 3 days a week in-office)
  • Alternate location: Open to candidates living in València, Spain
• Salary Range for Chicago: $120,000 – $150,000, plus eligibility to participate in a performance-based bonus program.
  • Estimated Total OTE: $150,000 – $187,500+
• Benefits: Medical, dental, vision, EAP, 401(k) match, ESPP, life and disability insurance, FSAs, flexible PTO, and more.