Director of Sales Enablement in Chicago, Illinois at YCHARTS INC

The Company

YCharts empowers wealth managers to make smarter investment decisions and communicate with confidence. Our SaaS platform combines powerful research, proposal generation, and client communication tools that transform complex financial data into clear visuals and actionable insights.

For nearly a decade, YCharts has been recognized on the Inc. 5000 Fastest Growing Companies list — a testament to our sustained growth, strong culture, and industry-wide impact. Thousands of leading RIAs, asset managers, and broker-dealers use YCharts to turn data into decisions, insights into action, and client conversations into growth.

A player-coach who builds and runs the program hands-on rather than through a team. The Director title reflects the seniority the role requires to operate: it needs to earn credibility with VP-level sales leaders across Institutional/Asset Management and Wealth Enterprise, own a platform, and represent enablement in company-level planning. As our sales enablement function continues to grow, this role will evolve to include building and leading a team, with the opportunity to shape the broader function, programs, and strategy along the way.

This role exists to turn YCharts' brand and product story into materials that sales teams use to win by focusing on value. Replacing today's sales resource center with a governed enablement library and program that measurably shortens sales cycles and improves win rates at the accounts that matter most. It is accountable for making enablement a trusted, trackable system.

• Own the sales enablement content library and platform, leading the evaluation and implementation of a tracked, tiered content system (a Highspot-class platform) to replace the current sales resource center, with content organized by segment and deal stage.
• Translate YCharts' brand promise and positioning into segment and persona-specific value-selling narratives and materials for Institutional/Asset Management and Wealth Enterprise sales teams first, then extend the same discipline to Key Accounts and Independent/SMB as the program matures.
• Partner with Product Marketing on positioning, competitive intelligence, and launch messaging inputs, and take ownership of turning those inputs into field-ready assets such as sales decks, battlecards, objection handling, and value/ROI tools.
• Build and maintain buying-committee content for complex, multi-stakeholder Institutional and Enterprise deals, working with sales leadership to identify the roles and objections each deal needs to address.
• Define and roll out a value-selling enablement and certification approach for segment sales teams, tied to the unified brand promise coming out of recently kicked off brand and positioning workstreams.
• Support ICP-tightening documentation in partnership with Product Marketing, Sales, and Demand Generation, so enablement content and targeting criteria are grounded in the same definition of a good-fit account.
• Partner with Marketing Operations and Demand Generation to define and track content usage and impact metrics including engaged selling time and content's influence on closed deals.
• Manage the sales enablement platform vendor relationship, implementation, and budget, including the business case for platform investment and the ongoing content governance model.
• Develop and execute a comprehensive sales adoption strategy that focuses on high-impact initiatives, create hands-on learning experiences, incorporate tracking and competition to drive engagement, and equip sales managers with the necessary coaching tools to ensure ongoing accountability across teams.

• Launch a centralized, tagged sales enablement library (interim hub or platform) with content organized by segment and stage, by the end of the first two quarters.
• Ship value-selling narratives and materials for the Institutional/Asset Management and Wealth Enterprise segments, tied to the unified brand promise, with adoption visible through platform usage data.
• Establish a first credible baseline connecting enablement content usage to sales outcomes (engaged selling time, content-influenced win rate), since no such tracking exists today specific improvement targets should be set once this baseline and the 2027 plan's broader attribution work are in place.
• Hold or improve conversion/win rate in the segments this role serves first, and improve marketing content development efficiency, consistent with the metrics the 2027 plan's headcount table assigns to this role.

• 8+ years of sales enablement, revenue enablement, or product marketing experience in a high-growth B2B SaaS environment, ideally within fintech, wealth management, or financial services software.
• A player-coach who builds and runs the program hands-on rather than through a team. The Director title reflects the seniority the role requires to operate: it needs to earn credibility with VP-level sales leaders across Institutional/Asset Management and Wealth Enterprise, own a platform, and represent enablement in company-level planning. As our sales enablement function continues to grow, this role will evolve to include building and leading a team, with the opportunity to shape the broader function, programs, and strategy along the way
• Executive presence and cross-functional credibility to effectively collaborate with and influence VP-level sales leaders across segments.
• Hands-on expertise with sales enablement platforms (e.g., Highspot, Seismic, Showpad, Dock), including evaluation, implementation, content taxonomy tagging, governance, and vendor management.
• Demonstrated success crafting value-selling narratives and field-ready assets, such as segment-specific sales decks, battlecards, objection handling scripts, and buying-committee enablement materials.
• Experience driving sales adoption & coaching strategies, including creating hands-on learning, engagement/incentive tactics, and actionable manager coaching toolkits that ensure team accountability.
• Data-oriented approach to enablement metrics, with experience establishing baselines and tracking content utilization, engaged selling time, and content-influenced deal outcomes.
• Strong cross-functional alignment skills, with a proven history of partnering with Product Marketing, Demand Generation, Marketing Operations, and Sales Leadership.
• Bachelor’s degree in Marketing, Business Administration, Finance, Communications, or equivalent practical experience.

• 100% employer-paid health, dental, and vision insurance.
• 401(k) match to support your financial future.
• Opportunities for internal mobility and cross-functional collaboration.
• Flexible time off, vacation days, sick days, and a celebration day.
• Paid parental leave to support work-life balance.
• Professional development stipend to help you grow in your career.
• Hybrid work schedule with flexibility to work both in-office and remotely.
• Summer hours so you can enjoy more sunshine.
• Recognition programs to celebrate contributions and milestones.
• Modern, centrally located offices stocked with premium snacks, coffee, beverages and weekly lunch credits to fuel your day.
• Regular team events, celebrations, and company-wide gatherings that keep our culture connected and collaborative.

At YCharts, we are committed to pay equity and transparency in all locations, including compliance with local pay disclosure requirements: the Total Cash Compensation range is $150,000-185,000 USD inclusive of bonuses and variable compensation. The starting salary will be determined based on skills and experience.

Why Join YCharts

YCharts is more than a fintech company—we’re a team driven by curiosity, collaboration, and people-first leadership. We believe innovation thrives in an environment where ideas are heard, growth is supported, and impact is measurable. Our award-winning culture reflects that commitment:

• Inc. 5000 Fastest Growing Companies (nearly a decade running)
• Crain’s Best Places to Work in Chicago
• Inc. Best Places to Work
• Built In Chicago Best Places to Work
• American Banker Best Fintechs to Work For

At YCharts, you’ll do meaningful work, grow alongside a talented team, and see the results of your impact every day.

YCharts is an equal opportunity employer. We celebrate diversity and are committed to fostering an inclusive, equitable environment for all employees.

Be part of the team transforming how the wealth management industry makes and communicates investment decisions.