Focused on extending the life and value of client websites, Cheeky Monkey Media is a Kelowna, BC-based web development agency specializing in website maintenance and upgrades. Our goal is to help our clients evolve their digital presence through ongoing web management, helping them avoid the constant redesign and rebuild cycle every few years.

We’re looking for an Outside Sales Executive to join our team, sell ongoing web maintenance services, and help us grow our client portfolio. This role is for the driven sales go-getter. The ability to hit the pavement, break down doors, and generate leads and opportunities will be keys to success in this role. As we work towards building a brighter tomorrow, we need a sales professional that can handle the hard work today.

You’ll be working with a passionate team of developers, designers, and marketers who all share a common goal, a weird sense of humour, and more than a little sass. If you’re a sales hunter who’s not afraid to pick up the phone, then you’re the person we want to add to this crazy team.

Job Responsibilities:

Business Development

  • Establishes new accounts by planning and organizing daily work schedules and activities to call on potential sales prospects and leads.

  • Prepare sales action plans and strategies

  • Generate and qualify leads

  • Focuses sales efforts through active, high-volume prospecting.

  • Respond to sales inquiries by phone, electronically or in-person

  • Develop and maintain a customer database

  • Follow up on sales activity

Sales Presentations

  • Develop and make presentations of company services to potential clients

  • Write & develop sales proposals (typing skill a definite plus)

  • Negotiate with clients and prospects

  • Prepare and present sales contracts

Reporting & Tracking

  • Keeps management informed by submitting activity and results reports, such as daily call reports, weekly work plans, and monthly tracking.

  • maintain sales activity records and prepare sales reports

  • monitor and report on sales activities and follow up for management

Team Contribution

  • Contribute to the development of sales and promotional materials

  • Plan and conduct direct outreach activities

  • Monitor competition by gathering current marketplace information on pricing, products, new products, delivery schedules, and merchandising techniques.

  • Recommend changes in products, service, and policy by evaluating results and competitive developments.

  • Maintains professional and technical knowledge through ongoing education, workshops, reviewing professional publications, and establishing personal networks

  • Participate in relevant events

Key Skills and Competencies

Personal Skills

  • Self-confident and highly motivated

  • Resilient and tenacious

  • High level of stress tolerance

  • Competitive and goal-driven

Sales Talent

  • Sharp Prospecting desire and skill

  • Planning and strategizing for high-volume outreach

  • Ability to use multiple avenues and tactics to generate contacts, leads, and opportunities

  • Demonstrated ability to meeting aggressive sales goals

  • Keen ability to recognize buying signals and close sales deals

Communications & Learning

  • Adept at deal negotiation

  • Verbal and written communication skills, outstanding phone skills (English as the first language)

  • Talent for sales presentations and conducting meetings

  • Ability to onboard quickly, develop product knowledge, and recognize solution elements

Education and Experience:

  • Relevant post-secondary degree (concentration in marketing, sales, advertising sales, or technology preferred)

  • Three to five years of sales experience and success

  • Familiarity with relevant computer applications

    • G Suite (Google Docs, Sheets, Presentations)

    • LinkedIn Prospecting

    • Yesware, MailChimp, Drip

    • Knowledge of digital sales platforms

  • General knowledge of digital marketing trends and technologies

  • NOTE: We’re seeking candidates that can demonstrate success in a highly competitive sales environment, regardless of industry. If you are new to the web but have significant sales experience and success, we want to hear from you.


Our head office is located in beautiful Kelowna, British Columbia, but this role is open to remote/work-from-home opportunities for the right person. Preference will be given to individuals in the Kelowna, Calgary, or Vancouver areas who can demonstrate a track-record for sales success in high-pressure environments.

Cheeky Monkey Media offers a competitive compensation package that includes salary, commissions, and bonuses, as well as paid time off and group benefits coverage.

This position is open to Canadian citizens and permanent residents. Please no agencies, outsourcing services, or individuals not legally able to work within Canada.