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Accruity, LLC is seeking a growth-minded Head of Sales & Marketing to own the front end of the funnel from first contact to Insights engagement. You will manage the 1099 sales reps, recruit and coach the team, and shape marketing strategy across paid social, content, and lead magnets.
You will partner with delivery to ensure seamless client handoffs and scalable growth. You will operate from Pittsburgh, driving demand in a fast-growing real estate investor-focused accounting firm.
At Accruity , we’re building something meaningful — for our clients and for each other. We’re a people-focused accounting services firm that helps business owners get back to what they do best by handling the financial heavy-lifting with clarity, consistency, and care. We support nearly 100 clients across the country with scalable, high-quality accounting solutions — and we’re just getting started.
We’re growing intentionally, investing in the right systems, structure, and culture to support great work and sustainable careers. Inside our team, we lead with trust, autonomy, and accountability — no micromanaging, no performative fluff. Just thoughtful self-starters doing real work, done well.
We believe the right fit matters most. We look for people who take ownership, invest in relationships, and aim to raise the standard every day. Our ideal teammate is reliable, curious, collaborative, and committed to growing — someone who welcomes feedback, takes initiative, and values being part of something bigger than themselves. If you’re always learning and believe how you show up matters, we think you’ll thrive here.
ACCRUITY
Accruity is a national, full-service financial firm built exclusively for real estate investors, real estate professionals and the businesses around them. We do bookkeeping, controllership, financial reporting, tax planning and tax strategy for operators who are building serious portfolios without a back-office team. We are operators and investors ourselves. We understand the world our clients live in because we live in it too.
We serve 140+ active clients across the country, and every one of them climbs the same ladder: a $1,500 Insights engagement that finds at least $15,000 of opportunity, a fixed-term build that gets their books and tax plan right, and an ongoing back-office relationship that keeps them there.
Accruity is backed by SteelPoint Capital Holdings — a Pittsburgh-based private investment platform founded by Casey Quinn, which owns and operates over $100M in real estate across 875+ units and lends to real estate investors every month. The people behind Accruity have skin in the game.
You own the front end of Accruity: everything from the first time an investor hears our name to the day they sign their Insights engagement. Demand, the sales team, marketing, and the affiliate and event engine — all of it.
Jeff Boscaino, our co-founder, runs delivery: the teams that do the work once a client is in. You own getting them in, at a predictable pace and a known cost. The division is clear, and the partnership between the two seats is what makes the model work.
The machine is partly built. There is a defined entry offer, a working sales script, two 1099 sales reps closing calls, a marketing manager, paid social, a CRM (GoHighLevel) and two activated affiliates. None of it is yet running at the pace the business needs. Your job is to make it run, measure it, and scale it.
1. Demand. The pipeline from first touch to closed Insights. Lead flow, strategy calls held, close rate, proposal turnaround. You set the plan, you run the weekly number, and you fix what is broken.
2. The sales team. The 1099 sales reps report to you. You recruit, enable, coach and hold them to the scorecard: every lead called within 24 hours, every meeting booked to the next, the CRM current within 30 minutes of a call. You personally close the high-value engagements that need a senior presence.
3. Marketing. Our Marketing Manager reports to you. You set the direction — paid social, content, our free framework guides and lead magnets, landing pages and funnels — and you hold every channel to a cost per closed client, not to clicks.
4. Affiliates, partnerships and events. We have two activated affiliates; we need twenty. You build the program, identify the right partners, activate them and measure what they send. You are in the masterminds, the investor events and the affiliate dinners, representing Accruity in the rooms where our clients are.
5. The handoff to delivery and the leadership cadence. A sale is only good if it becomes a client who stays. You work alongside delivery so that Insights clients move up the ladder, and you run the sales and marketing meeting rhythm — weekly scorecard, quarterly rocks — inside our EOS operating system.
Five numbers, reported weekly. Nothing else matters as much.
Qualified investors on a call with us, every week.
Insights closed and paid
The $1,500 entry engagement, sold and collected — the number the rest of the firm is built on.
Affiliate-sourced calls
Strategy calls that came from a partner, and the count of active partners behind them.
Marketing spend plus sales compensation, divided by Insights closed.
Ascension rate
The share of Insights clients who sign the build — owned jointly with delivery, because a sale that does not ascend was the wrong sale.
This is not a remote job. You are in Pittsburgh, in the office, and at the events, dinners and masterminds where relationships are built.
This is not a brand-management role. Awareness matters only when it shows up in strategy calls and closed clients.
This is not a delivery or operations role. You do not run the accountants. You make sure they have clients to serve, and the right ones.
Revenue you personally drove, with the funnel math behind it; a team that performed better under you; a channel you built from zero; a CRM you kept honest; a working knowledge of the real estate investor world.
your results are activity rather than revenue; you have never carried a number yourself; you have never built a referral program; you want to work mostly remotely; or you need a large team before you can produce.
Employment type: Permanent | Full-Time | Exempt
Reports to: Jeff Boscaino, Co-Founder & President
Compensation: $135,000–$155,000 base, commensurate with experience, plus variable compensation tied to Insights closed and new recurring revenue
Benefits: Medical (ICHRA, $300/month contribution) | Dental and Vision (Guardian, 100% employee premiums) | SIMPLE IRA with 3% match (Vanguard) | Company-issued laptop
Location: Pittsburgh, PA — in person, full time, with regular local and regional event travel