ContentFly (YC W21) : Head of Sales

Headquarters: Toronto, Canada


About the job

ContentFly (YC W21) is building the universal API for content creation – our vision is to allow anybody on Earth to get high quality content for their business in a few clicks. We haven’t done any sales to-date – yet, we’ve grown over 700% in the past 10 months profitably, and just raised a round of financing from some of the world’s top investors.

As the Head of Sales at ContentFly your role will be to build ContentFly’s sales function and playbook. In the early days you’ll focus on acquiring agency customers in parallel with building a team of high-calibre Account Executives and Business Development Representatives to assist you in your efforts.

We’re looking for a unique individual that is capable of handling the entire sales process from the first touch point to the final close. The right candidate will see this as an exciting opportunity to help build a sales organization from the ground up – which includes a lot of boots on the ground selling in the early days.


– Architect ContentFly’s sales playbook

– Hire, manage, and grow a sales team of high-calibre Account Executives

– Prepare sales forecasts and KPI reporting for the Leadership team

– Collaborate with your team and other functions within ContentFly to close large deals

– Provide full visibility into the sales pipeline at every stage of development

– Develop and execute on cold calling and email campaign strategies to qualify potential agency customers as a match for our outsourced content creation product

– Qualify outbound opportunities and develop a strong pipeline for our clients’ Account Executives via phone and email communications

– Meet weekly and monthly qualified opportunity goals to ensure client revenue objectives are met

– Learn and maintain in-depth knowledge of our system, sales industry trends, and competition

About you

– 5+ years of relevant technology sales leadership experience with a record of exceeding quota

– Possess extensive knowledge of sales methodologies and practices

– Strong analytical and quantitative skills; ability to use hard data and metrics to back up assumptions, recommendations, and drive actions

– Proven ability to influence cross-functional teams

– Entrepreneurial drive and comfort managing people as part of a team in ambiguous, quickly-changing environments

– Advanced knowledge of CRM and prospecting tools (Salesforce, Salesloft, ZoomInfo, InsightSquared, etc.)

Apply for the job

Do you want to join our team as our new Head of Sales? Then we’d love to hear about you!

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