Manager - B2B Sales Outreach (Accountant-Targeted Campaign)

 About Penbrothers 

Penbrothers is an HR & remote talent management partner and one of the fastest-growing companies in the Philippines. We provide talented Filipinos with global opportunities in high-growth startups and dynamic companies, from the comfort of their own homes.

About the Client 

The Client is a Canadian law firm focused exclusively on tax disputes: CRA audits, objections, Tax Court of Canada litigation, collections, voluntary disclosures and taxpayer relief. We handle high-stakes disputes with Canada’s tax authority and are deliberately breaking the traditional law firm mold in how we operate, market and grow: roughly 20 people within five years of launch, billings up approximately 170% from 2024 to 2025, and still scaling. Our Director of Business Development and Marketing is now building the marketing department, with most of the team based in the Philippines.

Work Hours: 9:00 PM to 6:00 AM Manila Time. May adjust in the future as outreach scales to Central and Pacific time zones.

About the Role

Accountants are the firm’s most important referral source: accountants at small and mid-size firms regularly have clients with CRA problems, and we want to be the firm they call. Rather than ask for referrals directly, we invite accountants to register for Taxpayer Law’s monthly tax disputes CPD program, presented by our lawyers; once registered, they hear from us all year.

The Call Centre Manager builds and runs the team that makes those invitations by phone, calling accountants at small and mid-size firms across Canada (excluding Quebec) and sending the registration link during or right after the call. The team starts with this manager.

This is a white-glove, high-ticket outreach team, not a volume call floor. The people on the other end are CPAs, and every call must sound like one professional calling another, not a telemarketer reading a script. The manager recruits, trains, coaches and runs the team, owns the lists and the numbers, and should expect to be on the phone personally in the first months. The Director sets the strategy, approves the call guides and owns the firm’s senior relationships with accounting firms; this role owns execution.

What You’ll Do

Building and Coaching the Team

• Hiring: Recruit, screen and hire the initial two callers with the firm’s staffing partner, assessing every candidate’s spoken English and phone presence personally on an unscripted call before hiring (the standard for callers is the same as for the manager); onboard, train, manage performance and replace callers who do not meet it.

• Call guides and coaching: Develop the call guides and objection handling with the Director and refine them from what the team hears. Coach through regular call reviews and side-by-side listening against a written quality standard.

Lists, Cadence and the Day to Day

• Lists: Build and maintain the call lists (accountants at small and mid-size firms across Canada, excluding Quebec) from public directories, firm websites and LinkedIn. Keep the data clean, record every outcome, and manage the recontact cadence so no firm is called too frequently.

• Running the program: Set daily and weekly targets and run the team to them; make calls personally during ramp-up and whenever the team is short or there is capacity; send registration links and follow-up emails promptly, in polished English, using templates approved by the Director.

Reporting and Systems

• Track dials, connects, conversations, registrations and attendance by caller and report monthly to the Director. Work with the Marketing Operations Manager on the dialer and CRM and keep registration and lead-source data flowing into the firm’s systems.

Compliance and Professionalism

• Apply and enforce the firm’s calling rules (the CRTC Unsolicited Telecommunications Rules, the National Do Not Call List and CASL for follow-up emails); the firm provides the guidance. The team represents a law firm at all times: courteous, discreet and confidential, with no pressure tactics.

What This Role Is Not

Not a volume call centre or BPO floor role: two callers, roughly 50 thoughtful calls each per day, measured on registrations and on how the firm sounds. Not an inbound intake, digital marketing, content, strategy or legal role: those sit with the Intake Coordinator, the SEO and PPC Managers, the Head of Thought Leadership, and the Director and the lawyers.

What You Bring

• C1 or C2 English proficiency level / Native-level spoken and written English with a neutral accent, assessed on an unscripted phone call, not a CV. Canadian accountants will judge you, and everyone you hire, within the first ten seconds of a call; this is the most important requirement.

• At least 3 years managing an outbound team calling North American, business prospects (B2B appointment setting, sales development or professional-services outreach). Consumer telemarketing, collections or inbound customer service does not qualify on its own.

• You have built a team from scratch: recruited and screened callers, written call guides, coached through call reviews and replaced people who did not meet the bar.

• You run a team on numbers and can show your previous team’s results.

• Comfortable running a team out of a CRM and dialer; polished written English for follow-up emails; willing to work a permanent overnight shift aligned to Canadian business hours, with the professionalism and discretion expected of someone representing a law firm.

 Nice to Have

• Experience selling to, or working alongside, accountants, lawyers or other professional services firms, and an understanding of what CPD is and why accountants value it.

• Familiarity with Canadian calling and anti-spam rules (CRTC rules, National DNCL, CASL); a network of elite English-speaking callers in Manila (premium North American B2B accounts, SaaS sales development teams); Lawmatics or a comparable CRM. 

Our Hiring Process & AI Disclaimer: We use AI tools to streamline our application process—including an initial conversation with an AI Interviewer. All hiring decisions are made entirely by humans: our Talent Acquisition team guides your full candidate journey and makes all evaluation decisions.

You are welcome to use AI for CV refinement and research, but real-time AI assistance during interviews or skill assessments is strictly prohibited to ensure an authentic evaluation. 

Read our full AI Disclaimer to learn more

 

What You’ll Get

At Penbrothers, we are obsessed with creating positive employee experiences. Here you’ll find an environment that nurtures learning and provides opportunities for growth. You’ll have the opportunity to make an impact on fast-growing startups and dynamic companies. 

·   Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience. 

·   Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.

·   Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home. 

·   Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.