Director of Revenue / Product Operations

Location: Chicago, IL
Job ID: 641724

Director of Revenue / Product Operations / Chicago, IL


Our client is a privately held company with 50 employees focused on North American sales. They offer the leading Home Inspection software for home buyers, inspectors, and investors. Everyone in the company all shares one thing in common: their passion for accelerating software innovation. Their vision is to put their solution in the hands of every new home buyer and residential home inspector in the United States. They are looking to expand their already 1,000,000 users per year and grow from owning 1/3 of the market today. They pride themselves on being an open and supportive company.

They support the remote employee experience. While we have great office spaces in Chicago and North Carolina they are very distributed and remote first (and always have been). They use a number of communication tools to connect across the company—and all remote employees have the opportunity to visit their offices and meet their teams face-to-face.

They value diversity and inclusivity. We offer perks such as parental leave, diversity, and inclusion working groups, and flexible working practices to allow our employees to show up as their whole selves. We are an equal opportunity employer and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

As the Director of Revenue Operations, you will report to the president of the company, own the Data Monetization product and help to create operational coordination between the teams. THIS IS NOT A SALES OPERATIONS ROLE! They have a cross-functional organization that is the foundation of the company’s sales strategy by evolving and uplifting their tools and infrastructure to drive and deliver exceptional operational results. This is not a Sales Operations role. As a leader, you will act as an advisor between, UI, Marketing, Partners, Sales, the Data team, and the customer while counseling and directing the organization toward strategic goals and operational effectiveness by meeting corporate sales, revenue, operational and strategic goals as well as the professional growth, development, and success of team members. You will have accountability to assist teams to improve performance across all departments. Think: Cross-functional coordination! 

Your Impact

·       Revenue Operations Drives excellence in the use of sales applications and processes centered around the opportunity.

·       Forecasting, Pipeline Management, and Reporting Manages & Supports the global booking, forecast, and pipeline management process in conjunction with the Finance organization.

·       Commercial Approval and Risk Review Process Ensures that deals are evaluated correctly to manage risk, ensure appropriate approvals are obtained, facilitate alignment with finance and legal departments.

·       Key areas of responsibility

·       Partner with senior sales leadership to identify opportunities to simplify the sales process through optimization and automation. Facilitate successful implementation and adoption of new processes within the sales organization. Foster an organization of continuous process improvement.

·       Design, implement and manage sales forecasting processes that provide accurate prediction into future bookings performance. Ensure forecasting efforts are appropriately integrated with other planning processes within the company.

·       Work with Human Resources, Finance, and senior sales leadership to design sales incentive compensation programs that provide market-competitive pay, reinforce sales organization strategy, and align with business and sales organization objectives.

·       Collaborate with Finance to assign sales quotas and other sales objectives to ensure the company’s financial goals are allocated to all sales channels and resources.

·       Own global deal desk; providing support in pricing, deal analysis, deal structuring, negotiation, and closure.

·       Assist all sales channels in overcoming business challenges to ensure ease of doing business while ensuring deal closure and revenue recognition.

·       Ensure that all sales tools accurately represent information and are effectively utilized by the team to process transactions and provide information about the status of the business.

·       Establish and implement performance measures designed to track and report progress against the global sales strategy.

·       Lead the Business Development/Inside Sales Teams ensuring alignment across marketing, sales, and BD

·       Lead Sales Enablement programs built to standardize onboarding, shorten ramp times, and ensure that the field is always armed with the most up to date and relevant information required to be successful.

Your Experience

·       Listen, this role is essentially the right-hand man or woman to the CEO.

·       You need to have some experience with providing strategic guidance and operational oversight in Operations within a technology sales environment.

·       Proven experience integrating SaaS tools, Data, advertising, and marketing to streamline and automate the sales process, integrating data science and analytics into every function within Sales to ensure greater predictability and productivity.

·       Experience building models for Annual Operating Planning: Bookings, Capacity, Quota, Compensation, Pipeline, Forecast, etc. would be a huge plus!

·       Experience developing, managing, and administering sales compensation models, cost structures, & plans and an ability to develop tactical initiatives that improve productivity and performance.

·       Background of introducing performance metrics and improvement programs.

·       Strong communication skills and ability to establish credibility and trust with all cross-functional departments, building influential relationships with all internal partners: Finance, Legal, Marketing, HR, Alliances, Support, Product Marketing, Professional Services, etc.

·       Understanding of both business and people, including their drivers and success factors.

·       Excellent knowledge of software pricing and licensing practices.

·       Understanding of sales methodologies and bookings process.

·       Highly entrepreneurial and able to operate independently with minimum supervision.

·       Heavily results-oriented; a strong track record in meeting and/or exceeding goals.

·       Able to research, develop and execute sales tools and strategies in the field.

·       Solid understanding of CRM systems, quote to cash management infrastructures, and analytics around sales pipeline modeling.

·       Deep knowledge/understanding of (including CPQ) is a must.

·       Familiarity with other potential tools, i.e., Yesware, ZoomInfo, Linkedin Navigator, Drift, HighSpot, Lessonly, InsightSquared, Olono, Zoom Conference Meetings, DocuSign, HubSpot, DemandBase, Sendoso


About the search firm running this search:

A Recognized Recruiting Leader in Enterprise Software.


Sourcing top talent is a lot more than just filling seats. It’s about identifying the best and brightest the industry has to offer and matching your needs with their wants in a career change. We leverage the candidate’s talents to enhance your company's long-term success. As a full-service executive search firm for the information technology sector, Woodbridge World Wide knows what it takes to attract and retain top talent in a changing business landscape. When you become our client, we strive to recognize what you are looking for in your hire/s and also take the time to learn the process that you would like to follow. Our founder worked in the industry in a sales capacity. He knows what it takes to be successful and what it takes to hit a sales quota. We understand what it’s like to make a career change and can relate our own life experiences to the candidate and client alike. Woodbridge World Wide provides retained, contingency and priority search services for all client-facing positions in the IT niche. As our client, you can expect consistently superior service delivered with the core value of our company: Partnership!



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