VP, Revenue Operations & Sales Enablement

We are seeking a strategic and visionary Vice President of Sales Operations and Revenue Enablement to lead our sales operations, enablement, and revenue strategies. This senior leadership role will work with the Chief Sales Officer and other teammates to drive the end-to-end management of SalesForce for both sales and service functions, as well as our lending platform, drive a comprehensive sales enablement program, oversee the Contractor Experience and Solutions Consultant, and align sales, marketing, and account management to maximize revenue growth, efficiency, and scalability in the point-of-sale financing space.

The ideal candidate is a forward-thinking leader with meaningful experience in point-of-sale lending, B2B, and B2B2C markets, a proven track record of leveraging AI and advanced analytics, and extensive experience leading teams and thriving in client-facing environments. They must excel at managing multiple work streams and projects while partnering closely with technology, risk, product, marketing, sales, account management, service, operations, and the Project Management Office (PMO). Reporting directly to the Chief Sales Officer, this position offers a competitive compensation package, including a base salary and performance-based incentive.

RESPONSIBILITIES

• Salesforce.com Ownership: Oversee end-to-end management of Salesforce.com for sales and service, and the lending platform, including configuration, customization, data integrity, user adoption, and integration with tools like ZoomInfo, Microsoft Power BI, and other platforms to support revenue and customer operations, as well as risk, ops, and lending.
• Sales Operations Leadership: Design and implement scalable sales processes, including lead management, pipeline forecasting, territory planning, and quota setting, to drive efficiency and predictability in revenue outcomes for point-of-sale financing solutions.
• Sales Enablement Strategy: Lead the development and execution of a comprehensive sales enablement program, delivering training, content (e.g., pitch decks, playbooks), tools, and coaching to empower sales teams to effectively sell financing solutions in B2B and B2B2C contexts.
• Contractor Experience and Solutions Consultant Oversight: Manage and guide the Contractor Solutions Consultant, ensuring seamless contractor and borrower experiences, technical sales support, and effective communication between sales, project management, and external partners to drive client satisfaction and platform adoption.
• Revenue Operations Alignment: Foster alignment across sales, marketing, and account management to streamline the revenue cycle, from lead generation to customer retention, ensuring a cohesive go-to-market strategy tailored to the home improvement industry.
• AI and Technology Innovation: Spearhead the adoption of AI-driven tools (e.g., predictive analytics, conversational AI, sales automation) to enhance lead scoring, personalize outreach, and optimize sales and service workflows, positioning Watercress Financial as a leader in innovative sales models.
• Data-Driven Decision Making: Leverage Microsoft Power BI, Salesforce.com, and other analytics platforms to deliver actionable insights, track key performance indicators (KPIs) such as conversion rates, sales cycle length, and customer satisfaction, and drive continuous improvement in revenue performance.
• Future Sales Models: Develop and pilot innovative sales strategies, such as account-based selling, subscription-based financing models, or hybrid B2B/B2B2C approaches, to anticipate market trends and drive sustainable growth in point-of-sale lending.
• Client-Facing Leadership: Act as a key representative in client-facing environments when necessary, engaging with contractors, partners, and key stakeholders to build trust, demonstrate value, and strengthen partnerships in the home improvement financing space.
• Team Leadership and Development: Build, lead, and mentor a high-performing sales operations, enablement, and Contractor Experience and Solutions Consultant team, fostering a culture of innovation, accountability, and collaboration while driving team engagement and career growth.
• Cross-Functional Collaboration: Partner closely with technology, risk, product, marketing, sales, account management, and the PMO to align strategies, ensure platform enhancements meet client needs, mitigate risks, and deliver cohesive business outcomes.
• Multi-Stream Project Management: Effectively manage multiple work streams and projects, prioritizing initiatives, aligning resources, and ensuring timely execution across sales operations, enablement, and contractor experience functions.
• Process Documentation and Scalability: Ensure all sales operations, enablement, and service processes are thoroughly documented (using Microsoft Office Suite) and accessible, enabling scalability and knowledge transfer across the organization.
• Performance Optimization: Continuously assess and refine sales, service, and contractor experience processes, tools, and training programs based on feedback, market trends, and performance data to maximize efficiency and revenue impact in B2B and B2B2C markets.

QUALIFICATIONS

• Bachelor’s degree in Business, Finance, Marketing, Communications, or a related field required.
• 8+ years of experience in sales operations, revenue operations, or sales enablement, with at least 4 years in a senior leadership role, ideally in point-of-sale lending, financial services, fintech, or B2B/B2B2C industries.
• Expert-level proficiency in Salesforce.com administration and optimization for both sales and service functions, including custom objects, workflows, dashboards, and integrations with tools like ZoomInfo and Microsoft Power BI.
• Proven track record of implementing AI-driven tools and advanced analytics to enhance sales performance, lead generation, service delivery, and forecasting accuracy in point-of-sale lending or similar markets.
• Extensive experience leading and mentoring high-performing teams, including roles like Contractor Experience and Solutions Consultant, fostering a culture of collaboration, accountability, and excellence.

KNOWLEDGE AND SKILLS

• Strong comfort and success in client-facing environments, with the ability to build relationships, articulate value propositions, and represent the company to contractors, partners, and stakeholders.
• Demonstrated ability to manage multiple work streams and projects, prioritizing effectively and collaborating with technology, risk, product, marketing, sales, account management, and the PMO to drive business outcomes.
• Deep understanding of sales enablement best practices, including training program development, content creation, and coaching methodologies tailored to B2B and B2B2C sales cycles.
• Strong knowledge of revenue operations principles, with experience aligning sales, marketing, and account management to drive end-to-end revenue growth.
• Forward-thinking mindset with a vision for innovative sales models, such as account-based marketing (ABM) or technology-driven strategies, to anticipate market evolution in the home improvement financing sector.
• Exceptional leadership and communication skills, with the ability to influence cross-functional stakeholders and present strategic insights to C-suite executives.
• Analytical expertise in using data visualization tools (e.g., Microsoft Power BI) and CRM platforms to drive decision-making and measure enablement impact.
• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint) for documentation, presentations, and process management.
• Experience with additional sales enablement tools (e.g., LinkedIn Sales Navigator, Highspot, Gong) and AI platforms (e.g., Gong, Clari, Outreach) is a plus.
• Ability to thrive in a fast-paced, dynamic environment, with a focus on scalability and operational excellence.
• Remote with occasional travel as needed, predominately to Des Moines, IA.