Directive

Head of Sales - Remote US

Directive Chicago, IL

Directive Consulting is the performance marketing agency for SaaS companies. We use Customer Generation (a marketing methodology developed by us) which focuses on SQLs and Customers instead of traditional metrics like MQLs. We offer Paid Media, SEO, Design/CRO, Video, and Marketing Ops services to our SaaS/tech clients.

We have experienced significant growth over the last few years and have remained true to our culture of, the best idea wins. We’re future-focused and are looking for the right Head of Sales to evolve and mature our sales organization.

About The Role

We have a mature sales process at Directive that balances a high-volume inbound with 100k+ ACVs. We follow the principles of Winning By Design, but have innovated to elevate our close rates and reflect the strategic differences in a services business vs tech.

In this role, you would own the pipeline, bookings and proposals held goal, and be intimately involved in the sales pipeline on a daily basis. Our CEO is also actively involved in sales calls on a daily basis and functions as our head of growth. You will be working and reporting directly into him.

A core opportunity for this position is the development of outbound sales practices by AEs. We do a full day of outbound weekly, but have struggled to get true leverage with our time.

In addition, we have events live under sales and expect you to travel heavily throughout the year. This is a core function of the role. We have 10+ private events a year and 10+ conferences. You need to attend + lead these events with support from marketing.

We have five total product lines: Paid Media, SEO, Design, Marketing Ops, and Video/Creative. In addition, we have a startup package that is experiencing double digit monthly growth.

To be a strong candidate, you need to be a marketing expert and understand the outcomes each service drives for SaaS companies and be able to predict with a high degree of confidence if the proposed strategy (in the pitch by your team) will exceed the client’s objectives. We are a unique blend of high volume inbound sales paired with deep, custom pitching/solution selling.

A crucial part of this role will be managing the sales team. You will have 4 direct reports (3 sr. AEs + 1 inbound SDR) across new business and will report directly into the CEO.

We value your ability to influence the pipeline as an individual contributor and believe that the ideal candidate revels in hopping on calls and attending events as much as they enjoy updating a forecast + diving into the data.

You will only be successful in this role if you are equally strong with sales as you are at performance marketing.

Roles & Responsibilities

  • Own the outcome of our pipeline
  • Have a deal strategy for every open opportunity
  • Build out enterprise sales playbook and travel to pitch in-person
  • Attend 10+ conferences annually
  • Attend 10+ private dinners annually
  • Manage 4 direct reports (New Business AEs + Inbound SDR)
  • Be involved in daily sales calls
  • Own the sales forecast and work cross-departmentally with operations
  • Deep technical knowledge of Paid Media, SEO, Design, Marketing Ops, and Video/Creative for SaaS companies
  • Strong SaaS background and expertise
  • Skilled at having a large impact in a very specific role
  • Creative spark for marketing + deep understanding of business & finance

What You Offer

  • 10+ years of experience in agency sales leadership
  • 5+ years of experience in performance marketing
  • Brilliant strategist and a truly T-shaped marketer
  • Sophisticated executive who understands finance, buying centers, enterprise selling, events, and working alongside agency operations

Benefits

  • 🙏 Medical, dental, vision plans, disability, and life insurance coverage for you and your family that fit your lifestyle
    • Including a 100% employer-paid plan for you and a 50% employer contribution for your dependents
  • Benefits to Support the Whole Person:
    • 🧠 Mental - Access to certified therapists through Spring Health, membership to Headspace
    • 💪 Physical - Physical therapy through Omada, fertility support through Carrott, thousands of Aaptiv virtual workouts, complimentary One Medical membership for primary and virtual care
    • 🛫 Time Off - Unlimited PTO (2-week minimum), Paid Company Holidays, Your Birthday Off, End of Year Recharge (Closed December 24 - January 1), Paid Parental Leave
    • 💰 Financial - Traditional and Roth 401(k) with a 3% company match
    • 🌟 Bonus - Annual bonus based on tenure, which scales in total amount over time
Work Environment Requirements

As a remote-first company, you’ll have the ability to work from anywhere in the US, with the option to enjoy our state-of-the-art offices in Irvine, California. For some positions, as posted, we will accommodate global opportunities where we have established businesses, including Canada, the UK, and Australia. For global locations, you must have established and current work authorization and permanently reside in that country.

This role has the opportunity to operate 100% virtually from your home office. We primarily collaborate with our colleagues through virtual meetings (Zoom), and Slack. In this role, you will be required to operate a laptop computer (PC or Mac available), computer software platforms, and other office productivity tools as necessary. Due to the nature of this role, you must be able to remain stationary for extended periods, must be able to observe and interpret written and/or verbal communication, must have reliable internet access, and a professional background.

To perform this job successfully, an individual must be able to perform each essential job duty satisfactorily. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform essential job functions.

If you require reasonable accommodations in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, direct your inquiries to careers@directiveconsulting.com.

Additional Information

At Directive, one of our core values is People First. We’re committed to fostering a more diverse and inclusive culture in the digital landscape. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status

  • Seniority level

    Executive
  • Employment type

    Full-time
  • Job function

    Sales and Business Development
  • Industries

    Advertising Services

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