Account Executive

Build relationships, generate pipeline, and own the full sales cycle for either Deer Brook's cybersecurity/audit/compliance practice or technology implementation/business consultive practices focused on higher education and ERP.

Deer Brook is looking for two Account Executives to build relationships and generate new business for our diverse practice areas. One position will primarily support our Technical and Cyber, Advisory & Professional Services teams. The other position will support our education and ERP technology practices, comprising implementation, digital transformation, and AI enablement.

You’ll combine outbound prospecting, consultative discovery, and relationship building to own each opportunity from first contact through signed agreement - working closely with our operations team to deliver solutions that solve real client problems. You will collaborate daily with our marketing team, with hybrid work opportunities available. No salary range has been established for this position.

What You’ll Do
Prospecting & Outbound

Research and prioritize target accounts across the technology, cybersecurity, software configuration and deployment market

Generate a majority of your own pipeline through outbound cold calls, emails, and social outreach

Qualify inbound and outbound leads against ideal client criteria

Act as a self-starter, consistently driving your own activity without needing to be prompted

Communication & Relationship Building

Build genuine, lasting relationships with prospects and clients, not just transactional contact

Serve as a clear, responsive point of contact throughout the sales process

Run discovery calls to understand a prospect's environment, risks, and business goals

Communicate clearly with both technical and non-technical stakeholders

Sales Cycle & Client Commitment

Translate client needs into a proposed solution and scope of services

Build and present proposals and pricing options

Run a full sales cycle: discovery calls, needs assessment, proposal or quote development, objection handling, negotiation, and closing - not solely lead generation or solely closing pre-qualified leads

Manage a multi-stage pipeline of simultaneous opportunities in the CRM, with accurate forecasting

Support a smooth handoff of signed clients to onboarding and service delivery

Marketing & Event Engagement

Take full advantage of marketing initiatives, campaigns, and content to fuel outbound efforts

Promptly follow up on inbound leads generated by marketing campaigns

Attend industry events, trade shows, and conferences to build relationships and generate new opportunities

Partner with the marketing team to identify events and campaigns worth prioritizing

What You’ll Bring
Required

Bachelor's degree in business, marketing, communications, or related field, or equivalent practical experience

Experience in outbound, relationship-driven sales, including cold calling and prospecting

Experience with a CRM tool for pipeline management and forecasting

A demonstrated self-starter who generates activity independently rather than waiting for direction

Located in proximity to Portland, ME or Charleston, SC

Strong communication and relationship-building skills, both verbal and written

Comfortable and effective making cold calls and sustaining high outbound activity

Skilled at handling objections and keeping conversations moving toward next steps

Ability to build clear, professional proposal and presentation materials

Preferred

Experience managing sales pipelines through use of a CRM, especially Microsoft Dynamics 365 Customer Experience

Experience with sales engagement or prospecting tools (Outreach, Salesloft, Apollo)

Prior experience representing a company at trade shows or industry events

Familiarity with one or more of Deer Brook's core markets - higher education, financial services (banks and credit unions), healthcare, defense/government contracting, and the non-profit sector

For candidates for the position supporting our Technical and Cyber, Advisory & Professional Services practices:

Cybersecurity and technology industry knowledge

Familiarity with compliance frameworks such as HIPAA and CMMC

For candidates for the position supporting higher education and ERP:

Familiarity with the software configuration landscape (e.g., common business systems, IT environments, or SaaS platforms) is a plus

Exposure to ERP or CRM platforms such as Microsoft Dynamics 365

Understanding of process automation and tools such as the Microsoft Power Platform

Accounting coursework or practical experience or past work in a college operations environment

Why Deer Brook
How We Show Up
We're guided by three behaviors that shape how we work:

Be There - We build trust through transparency, clear communication, and follow-through with clients and teammates.

Make the Move - We take ownership, act with urgency, and solve problems proactively rather than waiting for change to happen.

Choose the Better Way - We challenge convention, embrace new technology, and keep improving - for our clients and for ourselves.

What Success Looks Like
Consistently building relationships, generating pipeline, and owning deals end to end to grow revenue for Deer Brook's cybersecurity and managed services offerings - all while embodying these principles in every prospect and client interaction.

If you're excited about building relationships and driving new business, we'd love to hear from you.

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