About the Company
WordRake, headquartered in Seattle, WA is a software company dedicated to creating clear and concise editing solutions for professionals. Thousands of lawyers, editors, executives, marketers, and other sophisticated writers from AMLAW 100 firms, Fortune 500 companies, and government agencies use WordRake daily. The WordRake software was designed by lawyer, writing expert, and New York Times bestselling author Gary Kinder. It runs in Microsoft Word and Outlook, and its suggestions appear in the familiar track-changes style.
About the Team
We are a small team and our company is growing. We all juggle many roles and responsibilities and we have a deep appreciation for showing ownership and accountability. Every WordRake team member is committed to finding solutions and removing roadblocks. We believe in the value of every team member’s contribution, so no part of our company is off-limits for your suggestions and improvements.
About You
Do you love words, technology, and entrepreneurship—and wish you could find a way to combine all three?
We are looking for a sharp, driven person with a passion for great writing and clear communication—and the conviction that technology can help achieve those goals. The ideal candidate would use their entrepreneurial approach and passion for communication to help us create an effective enterprise sales process.
This may be the job for you if you:
  • feel confined by existing structure or process, but love making your own
  • thrive in a flexible, hands-off environment where you’re free to make your own playbooks
  • crave the opportunity to chase an ambitious goal and get rewarded for it
  • want to get promoted quickly with the potential to run your own team in 18-24 months
WordRake is the perfect company for hard-working, self-motivated people who want to chart their own course and experiment their way to success.
About the Role
We are hiring a sales representative to generate new enterprise sales. After onboarding, you will manage the entire sales process and be primarily responsible for identifying new sales opportunities and generating interest in our writing software. Your day will include prospecting and cold outreach, qualifying new business opportunities, running product demonstrations, creating proposals, and closing deals. Since you will be selling writing software and the role involves presentations, meetings, phone calls, and writing, excellent communication and listening skills are necessary.
This is a dynamic role that requires creativity, resilience, and drive to create new business opportunities. If you bring results, we will reward you for them, and we’ve structured our compensation to reflect that. If you are successful, you can expect to receive a salary increase and a title change three times in your first 18 months of work.
Joining the WordRake team is an opportunity to fast track your career in sales, so advancing a career in sales should be your main professional objective. But it is not required that you have direct experience in sales—we will give you a chance if you will give us your dedication and drive. If you are familiar with the sales process and you have experience developing new business systems and implementing them, then we will consider you.
You will sell writing improvement software to potential buyers across multiple verticals. Our highest concentration of users consists of legal professionals in North America, so you must be comfortable working within the legal world and you will be expected to develop relationships with ideal customers in it. The most successful business generators at WordRake use a consultative approach, and offer helpful resources and insight that will inform the buyer’s decision-making process, so you should have an interest in business or non-fiction writing, law, or business.
WordRake provides solutions that are compelling and make an immediate impact for our customers, so you’ll have the satisfaction of happy customers.
Your Personal Qualifications
  • Bachelor’s degree or higher
  • 2 years of experience in a professional office environment
    (internships count if they amount to 2 years of experience in under 4 years’ time)
  • Strong knowledge of Microsoft Office
  • Exceptional written and verbal communication skills
  • Great at building rapport and establishing relationships
  • Open, direct, and frequent communicator who is comfortable giving informal updates to executives throughout the day, every day
  • Positive can-do attitude and tireless work ethic
  • Unfazed by rejection and unintimidated by uncharted paths
  • Self-motivated and self-sufficient; hungry to succeed
  • Coachable and resilient
  • Willing to travel for trade events (up to 15%+ of time)
Key Qualifications for this Job
  • Tech savvy with the ability to confidently represent our product and quickly learn the technology involved with the sales and implementation process
  • Comfortable proactively engaging customers via phone, email, social media, and in-person
  • Detail-oriented and dependable, with the ability to prioritize and relentlessly follow up
  • Strong initiative, drive, and self-direction, with ability to work independently and as part of a team
  • Comfortable in a quickly changing environment and loosely defined procedures
  • Consistently reliable and accurate when recording sales activity to CRM
  • Strong presentation skills and the ability to deliver product demonstrations independently
  • Ability to communicate effectively at all organizational levels, including partner and non-partner levels, and with front-line law firm specialists and administrators
  • Ability to build meaningful relationships with internal and external stakeholders
  • Ability to navigate complex organizations and decision-making processes
  • Confident, quick-thinker, with the ability to influence and persuade
Key Responsibilities
  • Actively prospect to create new revenue opportunities and drive enterprise growth, identify and pursue new business opportunities, and increase sales within existing customer base
  • Build and manage the sales process from initial touchpoint through contract execution to meet and exceed individual and team goals; incorporate solution sales and consultative sales techniques
  • Test different outbound messaging tactics, measure performance, and adjust efforts accordingly
  • Qualify leads through prospecting: target research, cold emails, cold calling, and networking (social outreach and live events)
  • Demonstrate WordRake to potential customers and attend face-to-face meetings, as needed
  • Communicate the value proposition of WordRake’s solutions
  • Listen to, empathize with, and understand customer objectives, and articulate technology and business trends and benefits; stay current on industry trends and key personnel changes among prospect organizations
  • Answer prospects’ questions and offer content, including new product developments, based on their current needs or pain points; maintain active engagement with leads until they are ready
  • Coordinate calls and meetings with qualified leads and senior executives
  • Represent WordRake at events to influence sales opportunities
Additional Job Details
Company HQ: Seattle, WA
Work Arrangement: 100% Remote, Full Time
Base Salary: $40,000-$50,000 per Year
  • Months 1 to 6: $40,000 Base Annualized Earnings
  • Months 7 to 12: $45,000 Base Annualized Earnings
  • Months 13 to 18: $50,000 Base Annualized Earnings
Commission: 15% – No Cap; No Residuals; New Business Only
On Target Earnings: $60,000 to $90,000 per Year
Industry: Technology for Writing Improvement
Product: SaaS, Business Process Automation
  • Health and dental insurance
  • 10 days accrued PTO + 8 paid company holidays
  • Ability to mold your career and make an immediate impact
  • Monday to Friday
  • First three months must be 8 AM – 5 PM Pacific Time.
  • After first three months, you may choose to work a consistent schedule that fits within continental United States business hours
    (planned gaps or a split shift is allowed, so long as you work at least 8 hours per day)
About Our Hiring Process 
We understand that the best candidates may not have ideal resumes. We hope to look beyond biased expectations by asking questions to reveal your skills, interest, and motivation.  
We also understand that job searches require a lot of time for the candidate and the employer. We hope to create a process that is flexible enough to allow you to respond when it works for you and for us to get enough information to make the right decisions.  
We plan to have only one interview, which will be remote. We believe that by asking for more information now, we can limit real-time interviews during standard work days, and we will better respect your time. 
The process is intense and intentional. We look forward to getting to know you. 
About the Hiring Timeline
We will review applications on a rolling basis and we may hire someone before the deadline, so apply early. Our hiring process includes three phases and a final video interview: 
  • Phase 1: Initial Application and Questionnaire (Deadline: August 2 @ 4 PM) 
  • Phase 2: Product and Industry Questionnaire (Notified by August 9; Deadline: August 16 @ 4 PM) 
  • Phase 3: Written Role Playing Exercises (Notified by August 23; Deadline: August 30 @ 4 PM) 
  • Finalist Video Interview (Notified by September 3; Interviews week of September 6) 
  • Begin Training (Notified by week of September 13; Begin week of September 27 or October 4)