Outbound Sales Team Manager (Manager of Alpha Team)

Description:
Inspire Teams, Elevate Strategy — Deliver Lasting Impact

Annex Wealth Management – Know the Difference

Join Our Growing Team at our Headquarters in Brookfield, WI! (On-site gym)!

Are you in search of an employer that prioritizes a positive culture and encourages outstanding teamwork? ‘Know the Difference’ applies to our employees too. We are a proud seven-time recipient of the Milwaukee Journal Sentinel's Top Workplaces Award. Our employees list our vibrant culture and engaged teams as two of our best features!

Annex Wealth Management is a privately held, full-service advisory and wealth management firm acting as a fiduciary for individuals, families, and businesses. Our team approach means our clients consistently interact with a group of experienced professionals boasting key credentials, certifications, and achievements in investment, tax, insurance, estate planning, and more.

Communication and Education are key to Annex Wealth Management’s growth. Check us out on YouTube, our multiple podcasts, “Money Talk” on WTMJ; “The Investment Show” on WISN; and “The Annex Wealth Management Show” on WHBY and WFSX.

At Annex Wealth Management, our values aren’t just words – they guide how we work every day:

• Knowledge
• Accountability
• Integrity
• Courage
• Respect
• Ownership

Does this resonate with you? We're looking for positive, talented individuals who naturally embody these principles in their work and interactions. If you're ready to join a culture where these values are the foundation of everything we do, we'd love to hear from you.

About the Role

Crucial for driving outbound growth and digital engagement within the financial services industry; the Alpha Team Lead manages and elevates the performance of our Outbound Sales Team (Alpha Team). This role blends leadership, digital strategy, and content-driven outreach to drive growth, deepen engagement, and elevate team effectiveness. The ideal candidate is equal parts coach, strategist, and innovator. Comfortable leading people, building campaigns, leveraging CRM and digital tools, and adopting emerging technologies in a dynamic, fast-paced environment.

Key Responsibilities

• Team Management & Collaboration: Lead, manage, and mentor a team of outbound sales specialists, fostering a culture of accountability, performance, and collaboration. Set clear expectations, coach team members to meet and exceed KPIs, and conduct ongoing performance evaluations. Partner with internal stakeholders (marketing, advisory teams, leadership) to ensure cohesive messaging and alignment with organizational goals.
• Content & Campaign Development: Design, develop, and refine outbound sales campaigns that support lead generation, advisor engagement, and brand growth. Work closely with marketing to create messaging, scripts, email sequences, and content that resonates with target audiences. Continuously test, analyze, and optimize campaign effectiveness.
• Technology & Innovation: Leverage CRM systems (Salesforce and HubSpot) to structure workflows, monitor pipelines, and ensure lead quality and visibility. Incorporate data tools, databases, and reporting platforms to make informed decisions and improve sales accuracy. Champion the adoption and integration of AI tools to streamline processes, augment team performance, and enhance personalization.
• Digital Strategy & Execution: Build and execute digital outbound strategies using LinkedIn, email platforms, CRM automation, and other digital channels. Improve team proficiency on digital platforms to maximize reach and conversion. Stay current with digital trends and emerging best practices to maintain a competitive advantage.

Requirements:

What You’ll Need to Succeed

• Education: Bachelor’s degree in marketing, business, communications, or related field.
• Experience: Proven experience in digital marketing, including leadership or team management capacity. Background in wealth management, financial services, or insurance strongly preferred but not required.
• Tools & Technical Skills: CRM systems: Salesforce, HubSpot. Outreach platforms: LinkedIn, email automation tools. Data & reporting tools for campaign analysis and optimization. Familiarity with AI tools, with willingness and desire to expand their use within the team
• Communication & Collaboration: Exceptional communication, presentation, and leadership abilities. Strong analytical skills and the ability to interpret data to inform decisions. Ability to balance strategic thinking with hands-on execution in a fast-paced environment. Commitment to high levels of client and advisor engagement through digital outreach.
• Preferred Attributes: Self-starter with a proactive mindset and high comfort working in a fast-paced environment. Ability to balance strategic thinking with hands-on execution. Strong organizational skills with the ability to manage multiple campaigns and priorities simultaneously. Passion for helping clients and advisors succeed through digital engagement and relationship-building.

Comprehensive Benefits

We deeply value your leadership, talent, time, and commitment. In return, we offer a total rewards package designed to recognize and appreciate your contributions.

This includes a comprehensive suite of:

• Medical, Dental, and Vision Insurance
• Life & Disability Insurance
• Paid Time Off (PTO)
• 401(k) Retirement Plan: Build your future with our 401(k) plan and employer contribution
• Company Events: We believe in celebrating wins and creating connections – whether it’s through get togethers, our Annual Picnic, or company milestones
• Opportunities for professional growth and development
• Summer hours

We are committed to providing an environment where you can thrive and achieve your full potential.

Equal Employment Opportunity: Annex Wealth Management is an equal opportunity employer. We are committed to providing a work environment free from discrimination and harassment. All employment decisions are based on qualifications, merit, and business needs. We do not discriminate based on race, color, religion, national origin, sex, age, disability, genetic information, or any other protected status. We encourage applicants of all backgrounds to apply.