Mid-Market Cybersecurity Sales Leader

Cengage Group; Honolulu (HI); On-site; USD 67,000 - 87,000; Full time

Job summary

Cengage Group is seeking a hands‑on Mid‑Market Sales Manager to build and lead a team focused on converting inbound opportunities and generating new business through outbound prospecting. You will implement two complementary sales approaches while collaborating with Marketing, Enablement, and Revenue Operations to optimize pipelines and revenue growth.

The role emphasizes coaching, data‑driven decision making, and cross-functional collaboration to achieve quarterly and annual targets across the

Qualifications

• 5+ years of B2B sales experience, including at least 3 years of sales management experience leading quota‑carrying sales representatives.
• Demonstrated success managing teams responsible for both inbound lead conversion and outbound new business development.
• Proven track record of consistently achieving or exceeding team revenue and quota targets.
• Experience selling into mid‑market organizations, preferably within cybersecurity, technology, professional training, or B2B services.

Responsibilities

• Lead, mentor, and grow a team of inbound and outbound mid-market sales representatives to consistently reach individual and team revenue goals.
• Establish a culture of accountability, continuous improvement, collaboration, and high performance.
• Conduct regular one‑on‑one coaching sessions, pipeline reviews, deal strategy discussions, and performance evaluations.
• Develop representatives' capabilities in prospecting, discovery, objection handling, consultative selling, negotiation, and closing.
• Recognize areas of underperformance and apply focused coaching and growth strategies.
• Participate in recruiting, hiring, onboarding, and ramping new sales talent.
• Own the performance of the inbound sales motion, ensuring timely lead engagement, effective qualification, and strong conversion rates.
• Define and maintain clear expectations regarding lead response times, follow‑up intervals, opportunity management, and sales actions.
• Observe and optimize critical conversion metrics, including lead-to‑opportunity, opportunity‑to‑close, win rates, and average deal size.
• Collaborate closely with Marketing to assess lead quality, campaign effectiveness, lead volume, and conversion opportunities.
• Implement consistent sales processes that improve revenue from inbound demand.
• Support representatives in uncovering extra customer needs, growing deal value, and boosting overall customer experience.
• Establish and direct a forward‑thinking outbound sales process targeting the acquisition of new business in assigned mid‑market zones.
• Set clear expectations for prospecting efforts, account targeting, pipeline development, and opportunity identification.
• Coach representatives on effective multichannel prospecting strategies, including phone, email, social selling, and personalized outreach.
• Ensure representatives develop territory and account plans that prioritize high‑potential prospects and industries.
• Maintain steady pipeline growth to meet revenue goals and decrease reliance on inbound demand.
• Track outbound success by assessing activity levels, meaningful customer conversations, qualified opportunities, pipeline created, and revenue generated.
• Own overall mid‑market revenue performance, quota attainment, pipeline health, and forecast accuracy.
• Establish measurable benchmarks appropriate to the different inbound and outbound sales motions.
• Conduct weekly pipeline and forecast reviews to assess deal progression, identify risks, and improve close rates.
• Use Salesforce dashboards and reports to assess individual and group performance.
• Ensure strong CRM field, including accurate opportunity management, next steps, close dates, and forecasting.
• Detect trends and performance gaps and carry out actionable improvement plans.
• Drive consistent execution against monthly, quarterly, and annual revenue objectives.
• Complete the mid‑market go‑to‑market strategy aligned with Infosec's overall growth objectives.
• Work alongside Marketing to boost inbound lead generation, lead quality, campaign effectiveness, and sales conversion.
• Work together with Sales Enablement to strengthen sales approaches, onboarding, training, and continuous development.
• Work closely with Revenue Operations to optimize territories, lead routing, sales processes, reporting, and performance measurement.
• Partner with Customer Success and other sales teams to ensure effective account transitions and identification of growth opportunities.
• Provide market and customer feedback to help refine messaging, competitive positioning, and sales strategies.
• Continuously identify ways to boost sales productivity, efficiency, and scalability.
• Proficiency with Salesforce or a comparable CRM platform, including pipeline management, forecasting, and reporting.
• Strong communication, leadership, organizational, and problem‑solving skills.
• Ability to balance long‑term planning with hands‑on coaching and day‑to‑day sales execution.
• Experience partnering with Marketing, Revenue Operations, and Sales Enablement to boost sales effectiveness.

Skills

B2B sales experience

Sales management

CRM proficiency (Salesforce)

Inbound & outbound sales

Coaching & mentoring

Tools

Salesloft

Outreach

LinkedIn Sales Navigator

Job description

Cengage Group is seeking a hands‑on Mid‑Market Sales Manager to build and lead a team focused on converting inbound opportunities and generating new business through outbound prospecting. You will implement two complementary sales approaches while collaborating with Marketing, Enablement, and Revenue Operations to optimize pipelines and revenue growth.

The role emphasizes coaching, data‑driven decision making, and cross-functional collaboration to achieve quarterly and annual targets across the