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Make a great move


Chief Revenue Officer



Software Engineering
Toronto, ON, Canada
Posted on Wednesday, May 31, 2023
We are currently hiring full time in the following Canada locations: Ontario, British Columbia, Nova Scotia. If you are located outside of these provinces, you can still be considered as an applicant but the position will be on a contract basis.
About Plooto
82% of small businesses fail due to poor management of cash flow. Our vision is to enable the advancement of Small and Medium-sized Businesses (SMBs) by developing the tools & insights they need to maximize their cash flow. Over 10,000 businesses and their finance teams trust Plooto to automate their financial processes so they can focus on reaching their true potential.
Founded in 2015, Plooto raised $24M in Series B venture funding led by Centana Growth Partners in January 2023 and has multiple years of runway. The company has scaled 5X from the Series A to B raise while maintaining less than 1% churn.
Your Role
As our Chief Revenue Officer (CRO), you will own end-to-end revenue generation at Plooto. As the CRO, your main responsibility will be to enhance and scale our GTM strategy to drive rapid growth. You will build on our current revenue streams, as well as develop new ones and prioritize performance while keeping customers at the forefront of everything you do. You will oversee various functions, including Sales, Partnerships, Adoption, Customer Success, and RevOps.
Your Impact
Revenue Strategy: You will own the revenue strategy as we look to 10x our business over the next 3 years. You will focus on expanding on our existing channels, partnerships, and verticals, and creating new ones. You will continuously evaluate market trends, customer needs, and the competitive landscape to identify strategic opportunities to maximize our growth.
Business Development: You will drive new sales motions, including hybrid inbound/outbound, ABS, and partnerships. You will lead your team to develop and optimize the sales processes, forecasting, pipeline generation/management, and pricing models. You will partner with Growth Marketing to develop tailored content, campaigns, and events to engage our prospective customers.
Partnerships and Channels: You will work closely with our Enterprise and Channel Partnerships leaders to design and execute a strategy focused on the retainment, onboarding, referral, and ongoing management of our accounts. You will continuously assess partner performance and provide guidance to enhance our Partnership capabilities.
Sales Leadership: You will scale and foster a high-performing sales culture focused on revenue attainment through delivering value to our customers. You will establish aggressive sales targets, optimize continuously, and coach & mentor the team as we look to 10x our customer base.
Adoption and Retention: You will seek to expand our customers’ lifetime value through upselling, cross-selling, and retention initiatives. You will partner with the Adoption and Customer Experience teams to ensure world-class customer satisfaction, engagement, and retention.
Data and Reporting: You will continuously improve your insights by implementing comprehensive analytics and reporting systems to track key revenue metrics, sales performance, and ROI. You will deliver robust forecasting tools aligned with business objectives.
Your Background
Experience: You have a minimum of 15 years of experience with at least 8 years of experience in senior sales or revenue leadership roles within the SaaS or fintech industry. You have a deep understanding of the SaaS or FinTech industry and can clearly demonstrate a path to exponentially growing the customer base. You hold a Bachelor's degree in business, marketing, or a related field (MBA is preferred).
Business Development: You have developed and scaled multiple sales motions with a proven track record of business development, account management, and aggressive revenue growth. You understand the SaaS business model extremely well.
Data-Driven Decision-Making: We are a meritocracy, so you will find that our decisions are based on facts, not dispositions. You are obsessed with analyzing and leveraging data to set your strategy, gain buy-in, and communicate how to execute your plan successfully. You have a proven track record of operationalizing sales performance metrics, tracking, and reporting to drive greater visibility and insights.
Leadership: You have a reputation for being a coach and mentor. You understand how to drive teams to achieve big wins. You have deep experience in recruiting, developing, and scaling a high-performing sales team with accountability across revenue and growth goals. You are an exceptional communicator with the ability to influence and collaborate across departments.
Soft Skills: You embody Plooto's Leadership Principles and leverage them consistently in your work and leadership style. You are an avid learner looking to understand the hows and why from a data-driven perspective. You are not willing to settle for good; you are looking for excellence. Your bar is high! With an entrepreneurial mindset, you are not afraid to drive organizational change to achieve the overall Plooto goals. As an effective communicator, you can effectively communicate and collaborate at an executive and Board level.
Why Become a Plootonian?
If you are looking to make a professional impact, look no further. Plooto is currently in hyper-growth mode, looking to 10x our customer base. The biggest reason why SMBs close their doors is poor management of finances and cash flow. Plooto solves that problem! Plooto is dramatically changing the payment automation category in North America. Our unrivalled product experience fulfills a crucial need in the SMB segment. We have an extremely strong product-market fit with a massive opportunity ahead of us. An experienced and diverse group of FinTech veterans backs us. You will have the opportunity to make history and change the course of this sector for many years to come. Join Plooto and be a part of making history.