IT Outside Sales Representative

This is NOT a Fully Remote position.

This position can be partially remote, however there are required weekly in-office meetings and on-site visits with clients. There is space at our headquarters in Wauwatosa if someone desires a more traditional office environment.

The Outside Sales Representative is responsible for generating new business for Tobin Solutions through relationship‑building, consultative conversations, and participation in local networking and business events.

This is a technical sales role, ideal for someone with an MSP or engineering background who can speak credibly to business IT needs and partner closely with the Service Manager and engineering team.

This role is not marketing, and it is not high‑pressure sales although it is focused on proactively going out to generate new leads. It is a trust‑based, relationship‑first position aligned with Tobin’s values and Customer Bill of Rights (CBOR). The Outside Sales Representative becomes a face of Tobin Solutions in the Milwaukee community.

New Business Development

• Identify, cultivate, and qualify new business opportunities in the Milwaukee metro area.
• Attend and actively participate in networking events (MMAC, local chambers, industry meetups, referral groups).
• Represent Tobin Solutions confidently and professionally as a trusted technical advisor.
• Conduct discovery meetings to understand client goals, challenges, and budgets.
• Use a consultative, non-pushy approach centered on problem‑solving, not pressure.
• Translate client needs into clear, accurate proposals that align with engineering capacity and best practices.
• Collaborate directly with the Service Manager and engineering SMEs to validate scope, timelines, and security standards.
• Ensure all proposals reflect Tobin’s systemized approach and CBOR commitments (clarity, responsiveness, no surprises).

Pipeline & Relationship Management

• Maintain a healthy pipeline of qualified prospects through relationship‑building and consistent follow‑up.
• Document all interactions, notes, and next steps in Connect Wise accurately and promptly.
• Provide warm handoffs to the engineering and service teams after a sale is closed.
• Continue light‑touch relationship maintenance after onboarding to ensure long‑term satisfaction and future opportunities.

Internal Collaboration & Documentation

• Follow Tobin’s documentation standards — if it isn’t documented, it didn’t happen.
• Work closely with the Service Manager, Project Management, and engineering team to ensure a smooth delivery experience.
• Participate in internal meetings to align offerings, refine service bundles, and ensure our proposals match operational reality.
• Contribute ideas that improve the consistency, clarity, and repeatability of the sales‑to‑service handoff.

Brand Representation

• Attend community events as a visible, friendly representative of Tobin Solutions.
• Communicate Tobin’s values, quality standards, and CBOR commitments with confidence.
• Build genuine rapport that leads to trust, referrals, and future growth.
• Maintain a professional image and uphold Tobin’s culture of courtesy and responsiveness.

• 2+ years of MSP sales, technical sales, or IT engineering experience.
• Strong understanding of IT fundamentals (networks, cybersecurity, cloud, managed services).
• Comfortable engaging with new people, attending events, and representing the brand in the community.
• Experience collaborating with technical teams on proposals or client solutions.
• Highly organized with strong documentation habits.

• Experience with Connect Wise or similar PSA/CRM systems.
• Familiarity with ITIL concepts or structured service delivery frameworks.
• Strong local Milwaukee business network.
• Understanding of security frameworks and best‑practice alignment.

• Prospects feel heard, respected, and clearly informed.
• Proposals are accurate, realistic, and aligned with engineering capacity.
• Handoffs to the service team are smooth, documented, and complete.
• CRM notes are up‑to‑date and detailed.
• Prospect engagement feels human, not salesy.
• You become a recognizable representative of Tobin in the community.
• New clients onboard with clear expectations and no surprises.
• You consistently uphold Tobin’s VMV and CBOR in every interaction.
• Team Collaborator:
  You protect engineering time by selling accurately.
• Service‑Oriented:
  You demonstrate courtesy, clarity, responsiveness, and reliability.
• Systems‑Minded:
  You follow documented processes and help improve them.
• Technology Curious:
  You understand the “why” behind technical solutions.

• Entry level

• Full‑time

• Sales and Business Development