Account Executive


We’re on a mission to redefine the sales technology industry! This is challenging work – but our team of brilliant creatives makes the journey thrilling. We’re fast paced, innovative and collaborative. We pursue excellence in everything and have fun along the way.

About the Company:

InsideOut is a sales play development and experimentation company. We design, test, and install sales plays into our client’s native sales applications to increase buyer engagement through highly personalized Sales Plays. InsideOut works with large enterprise sales organizations to maximize the potential of their buyer engagement strategy by providing the strategic design, copywriting, and technical installation of sales plays into any native sales application. InsideOut has delivered over 12,000 sales plays into enterprise sales applications for over 50,000 salespeople that want to drive higher personalization across their sales engagement process.

Employee Benefits:

  • Health insurance premiums paid 100% by the company
  • 401(k) with 4% company match
  • Life insurance premium paid 100% by the company
  • 15 paid personal days off (vacation/sick)
  • 8.5 paid Holidays off
  • Ability to work with some of the world’s most advanced companies, acquiring a deep understanding of their sales processes, techniques, teams, and technologies
  • Professional development and sales skill mastery through internal and external training opportunities
  • The opportunity to join a fast-growing organization and experience rapid career growth

About the Role:

We are seeking a results-oriented, motivated, and strategic ‘hunter’ who is laser-focused on generating new business within North America. Specifically, you will play a pivotal role in helping us maintain and develop our position as a leader in sales optimization through innovation. You will achieve this by acquiring highly desirable clients and crushing your quota.

On a day-to-day basis, you will be responsible for educating the market about the power of InsideOut and generating net-new customer opportunities. You must be able to successfully forecast sales activity and revenue achievement while creating satisfied and referenceable customers. To thrive in this role, you will keep up with industry trends, competitive landscape, and client needs.

If you’re passionate about sales processes and technology, providing a world-class client experience, and thrive in a fast-paced, hyper-growth startup environment, then joining the InsideOut team is the right step for you!

*Note: Travel up to 25-40% of the time required


  • Create detailed account and sales plans to facilitate the attainment of your personal goals and quotas
  • Create, discover and qualify new sales opportunities through our partner network, direct response marketing and your personal network
  • Present InsideOut mission and services to prospective clients in-person and virtually to educate decision-makers, gain their trust and commitment to next actions required in the sales process
  • Manage the full sales lifecycle from prospect identification to new business “closed: won”, within all target segments assigned
  • Produce and deliver client facing proposals, quotations and detailed Statements of Work:
    • aligned to specific client needs
    • matching client needs to InsideOut’s product and service offerings
    • in accordance with InsideOut standards and pricing
    • through collaboration with CRO on proposition and positioning
    • Maintain strong lines of communication with business leaders, providing detailed insights into the sales pipeline
  • Keep records of all sales activities and engagement to include detailed notes and insights
  • Manage time and energy effectively between prospects, clients, and projects

*The duties, responsibilities, and conditions described are not necessarily a comprehensive list. Additional tasks and requirements may be assigned to the employee from time to time, as necessitated by business demands. Given the nature of the business, the company retains the right to modify the essential functions of this position at any time.


Skills and Experience You Possess:

  • Bachelor’s degree preferred
  • 3 years of proven hunting & closing experience in a SaaS environment required
  • Consistent overachievement of quota and revenue goals
  • Experience establishing and leveraging strategic C-level relationships
  • Prior experience having successfully managed a full sales lifecycle
  • Experience executing detailed product presentations and web demonstrations to C-level sales executives, VPs, directors, and managers
  • Advanced knowledge of Microsoft Office Suite (Word, PowerPoint, Excel)
  • Advanced knowledge of CRM software (Salesforce preferred)
  • Experience with Cadence Management software and other Sales Enablement tools (SalesLoft, Outreach, Drift, Gong, etc.) preferred
  • Excellent communication/presentation skills and ability to build strategic relationships
  • Excellent listening skills: you must understand objections and defeat them by turning skeptics into ecstatic new advocates
  • High level of empathy – it’s important for our AEs to be a good person to peers and prospects
  • Excellent organization and time-management skills
  • Highly collaborative – prioritizing ‘we’ and not focusing on ‘me’
  • Knowledge of market research, sales, and negotiating principles
  • Ability to understand InsideOut’s target account profile, quickly determining the best offer for the right customer to sell various pricing packages.

Offer Contingencies:

This role is contingent upon passing both a background check and a drug screening prior to employment (post-offer)

  • Employer check
  • Qualifications check
  • Right to work in the USA

Job Category: Sales and Marketing
Job Type: Full Time
Job Location: St. Petersburg - Florida