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Territory Sales Manager - Payroll/ HCM - Boston Metro

Remote, USA Full-time Posted 2025-05-22

Before applying, please note this is an OUTSIDE B2B SALES ROLE focused on Payroll and HCM products.

Due to growth and expansion in the area we are looking for an outside B2B remote Payroll/HR sales as a Senior Product Advisor (SPA). Experience in Outside Sales/ B2B Sales/ Hunting/ Relationship Management is a must. Proven and documented top performers only.

Honesty and integrity and be willing to do the right thing when nobody's watching. Tenacity to get out of your comfort zone. These are core values at Heartland.
• You have to be able to handle a 'no.'
• You must know how to directly ask for business.
• You must be dedicated to building a professional network.

Career Path: Territory Manager (Player/Coach) role.

As a Territory Manager you are responsible for assisting in the development of Senior Product Advisor (SPA) (outside B2B remote sales representative) by providing the following:
• Hands- on field support
• Mentoring and sales process training
• Expert product and industry knowledge
• Generate ongoing sales of new and existing customers
• Well versed in applying Heartland sales process implementation
• Strong focus on the training and development of Payroll Senior Product Advisors

Compensation-Benefits:

This is a W2, full benefits position selling payment processing as well as partnering with our Payments Division to up-sell our existing portfolio. First year professionals can expect an average of $90,000 - $105,000+ if you are in the top 25% in the form of uncapped commissions. Compensation includes weekly commission paid every Friday, monthly recurring residuals, and opportunity to own your portfolio!

Additional benefits include:
• Semi Annual Incentive Trips for Top Performers
• Stock options and prizes available for Top Performers
• Medical, dental and vision insurance
• 401 (k) retirement plan with company match
• Employee referral bonus program
• Voluntary life and AD&D insurance
• Healthcare Savings Account
• Voluntary Accident, Hospital and Serious Illness Insurance

Here's what you can expect at Heartland:
• 12-month upfront bonuses paid weekly;
• Lucrative compensation plan
• Uncapped residuals that build wealth monthly, while collecting on vested equity - even if you don't work at Heartland forever.
• Our training program ensures you get on track, stay on track and secure success.
• Use of Atlas, our groundbreaking iPad platform for lead generation, sales presentations, on the spot client financial analyses
• Remote work
• Travel is up to your own discretion
• Work / Life balance
• No limit on a territory within the United States

#2 - Overview

The Territory Manager is responsible for the sale of the organization's payroll and related products offered in a specified region or major geographical area. The Territory Manager will be assigned to a sales team within a geographic area to train, aid and assist in helping the Relationship Manager and Senior Product Advisor to sell our product either on their own or by way of referral so that the TM can sell it to the end user directly. The compensation is highly leveraged with the opportunity for creating passive income.

Role

Your role as a TM is to close sales of our payroll solutions with merchants throughout the area. As a TM with Heartland, you will work closely with your local Division to set appointments with business owners over the phone, face-to-face, through your network, and via referral partnerships that you build. You will then run scheduled appointments, uncover needs, and present Heartland solutions to close sales in our target vertical markets (restaurants, retail, medical, lodging, auto repair, salons, etc.).

During the training/ramp-up period, your local manager will accompany you on your initial appointments to train you on our short-cycle sales process using Atlas, our groundbreaking tablet-based CRM platform for lead generation, sales presentations, on the spot client financial analysis, and paperless contract processing. You will then have the freedom to set your own work schedule while working primarily from a home office and maximizing the upside of residuals and vesting opportunities.

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