Sales Development Representative 

Role Overview

Cannolai is seeking a highly motivated Sales Development Representative (SDR) to help accelerate our growth within the association and nonprofit market. As the first point of contact for prospective customers, you will generate qualified sales opportunities through outbound prospecting, inbound lead qualification, and pipeline development.

You will report directly to the CRO and work closely with our Sales and Marketing teams. Because we are early-stage, you will operate with meaningful autonomy and have visibility into the entire revenue operation. This role is ideal for someone who enjoys engaging with prospects, uncovering business challenges, and opening doors to meaningful sales conversations.

You might be a great fit if you are:

• Energized by outbound prospecting and talking to new people every day
• Naturally curious about how organizations operate and what problems they face
• Organized, self-motivated and self-starter, and comfortable managing your own pipeline
• Excited by the idea of growing into a closing sales role
• Drawn to mission-driven companies and the nonprofit/association sector

Key Responsibilities

Outbound Prospecting

• Identify and research target associations and nonprofit organizations using various prospecting tools.
• Build and maintain targeted prospect lists and execute multi-channel outbound campaigns via phone, email, LinkedIn, and other channels.
• Develop personalized, insight-driven messaging that resonates with association executives and key decision-makers.
• Generate qualified meetings and pipeline opportunities for Account Executives.
• Consistently meet or exceed activity targets and pipeline generation goals.

Inbound Lead Qualification

• Respond promptly to inbound inquiries generated through marketing campaigns, events, webinars, referrals, and website activity.
• Qualify marketing-qualified leads (MQLs) using established sales methodologies and qualification frameworks.
• Identify business challenges, project timelines, budget considerations, decision-making processes, and technology requirements.
• Route qualified opportunities to the appropriate Account Executive and maintain a positive prospect experience throughout.
• Provide structured feedback to Marketing on lead quality, messaging effectiveness, and market trends.

CRM & Pipeline Management

• Maintain accurate and up-to-date prospect and opportunity data within HubSpot.
• Track all prospecting activities, conversations, follow-up tasks, and next steps.
• Ensure data quality and adherence to established sales processes and naming conventions.
• Collaborate with Marketing to improve lead scoring, nurture sequences, and conversion rates.

Required Skills & Experience

• 2–3 years of experience in sales development, business development, inside sales, customer success, or a closely related role.
• Strong written and verbal communication skills with an ability to engage and build rapport quickly.
• Comfortable making outbound calls and engaging director- and VP-level executives.
• Demonstrated ability to manage multiple priorities, follow-up activities, and prospecting cadences simultaneously.
• Strong organizational and time management skills with a bias toward action.
• Experience using CRM platforms such as HubSpot, Salesforce, or similar tools.
• Self-motivated with a genuine desire to learn and grow in a sales career.

Preferred Qualifications

• Experience selling SaaS software, particularly to SMB or mid-market buyers.
• Experience selling to associations, nonprofits, or other membership-based organizations.
• Hands-on experience with HubSpot CRM and/or HubSpot Marketing Hub.
• Proficiency with prospecting and sales intelligence.
• Familiarity with sales methodologies such as MEDDIC.

Success Metrics

Performance in this role will be measured against the following key indicators:

• Qualified meetings scheduled with net-new prospects
• Sales-qualified opportunities (SQOs) created and passed to Account Executives
• Total pipeline value generated
• Inbound lead response time
• Outbound activity levels (calls, emails, LinkedIn touches per week)
• MQL-to-SQO conversion rate
• CRM data quality and process compliance scores

Benefits for Cannolai Employees 2026

Cannolai partners with TriNet to offer Fortune 500 Benefits and employer services.

Health & Life Benefits

• United Healthcare Medical Plan – multiple plans available, including low deductible; both in network and out of network coverage plans.
• Dental plan: TriNet provides multiple dental plans that you can customize to your own needs. There is an increased maximum annual benefit available and now there are plans offering orthodontic care
• Life Insurance: $50,000
• Vision: Multiple vision plans to choose from to fit your needs. Vision and Glasses exam; lenses/frames coverage and contacts allowance.
• Long/Short Term Disability: you can choose both long and short term disability benefits
• Personalized HR Management System where you can access and enroll in all benefits online, view and acknowledge companywide updates and policies, and go online and view personal information (banking information, home address, pay statements, tax filing etc.) Other Benefits Employee Perks – hundreds of discounts on cell phones, computers, electronics, clothing, movie tickets, theme parks and travel
• Unlimited Time Off – Cannolai offers Unlimited time off for all full-time employees

2026 Holiday Schedule:

• January 1, 2026 — New Year's Day
• January 19, 2026 — Martin Luther King Jr. Day
• February 16, 2026 — Presidents' Day
• May 25, 2026 — Memorial Day
• July 3, 2026 — Independence Day (Observed) (July 4, 2026 is a Saturday)
• September 7, 2026 — Labor Day
• October 12, 2026 — Columbus Day
• November 11, 2026 — Veterans Day
• November 26, 2026 — Thanksgiving Day
• November 27, 2026 — Day After Thanksgiving
• December 25, 2026 — Christmas Day

401k (Safe Harbor):

Cannolai offers a 401k plan to eligible employees. Under the Plan, eligible employees may elect to have a portion of their salary (up to IRS maximums) deposited directly into a 401(k) account. This pre-tax contribution is called a “Salary Deferral.” There is no income tax while Salary Deferrals are held in the Plan, and any earnings on Salary Deferrals are not taxed while they stay in the Plan.

· Matching: The Plan is known as a “Safe Harbor Plan” which offers employees a generous employee match according to the following matching formula.

· Eligibility: To be eligible to receive a Safe Harbor Matching Contribution, employees must complete 6 months of Service.

Professional Development:

Lifelong learning and continuing education is an important value of the Corporation. Accordingly, the company will fund training, conferences and certification courses which are approved in advance by the CEO.

Performance:.

Employees are entitled to an annual performance review performed by their immediate supervisor.

Pay: 

Pay days are bi-monthly (15th and last day of month).