Head of Sales Development Jobs
Head of Sales Development jobs are open across SaaS, fintech, healthcare technology, and enterprise software, at every level from team lead to vice president, with specializations in outbound strategy, pipeline generation, and SDR team management. Find a role that fits below and apply directly.
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Head of Business Development (Building Partnerships)
Full-time · Chicago, hybrid · Pentice / Cloud9 Windy City · Reports to the CEO
1. Role and mission
Mission: You sign more profitable Class A buildings for Pentice. You find, win, and close deals with the people who control these buildings. You own each deal from the first contact to the signed agreement.
Who you sell to:
Property management companies: They run many buildings. One relationship can open a full portfolio.
Regional managers: They control access to many buildings in a market. They often make the first recommendation.
Asset managers: They report to investors. They need proof that Pentice improves the return on hard-to-lease units.
Owners: They give the final approval on many deals.
Team: Business Development. You work closely with the CEO. Operations gives you the guest proof that you use to win deals.
2. Outcomes (scorecard)
You own these results in your first 12 months. You and the CEO set the values for X, Y, Z, P, and A from the plan.
Signed inventory
Sign Y new buildings or Z net new units in 12 months.
Each deal must meet or exceed our target contribution margin.
You close these deals. The CEO joins only on deals that the two of you select.
Portfolio deals
Sign P agreements with property management companies or asset managers. Each agreement must open 2 or more buildings.
Pipeline
Get X qualified decision-maker meetings each month by Month 6.
Track meetings by buyer type: property management company, regional manager, asset manager, and owner.
Make sure that 70% or more of meetings are about ICP buildings. ICP buildings are Class A buildings, or large units that do not perform well, in our target markets.
Deal speed and cost
Decrease the median time from first meeting to signed agreement by A%.
Set a target cost for each signed unit, then meet that target.
Proof for deals
For each signed building, capture 1 or more proof assets within 6 months. Examples are a case study, a financial result, or a testimonial. Use each asset in 3 or more active deals.
You will report these weekly KPIs: new contacts, first meetings, proposals sent, deals in negotiation, and contracts signed.
3. Key responsibilities
Build the target list. Map the Class A buildings in our markets. For each building, find the property management company, the regional manager, the asset manager, and the owner.
Open doors. Contact decision-makers directly. Use your network, referrals, LinkedIn, email, phone, and industry events.
Run the full sale. Lead discovery calls, building tours, proposals, and negotiations. Close the agreement.
Sell to each buyer differently. Give regional managers an easy yes. Give asset managers the financial case. Give owners confidence.
Win portfolios. Turn one signed building with a management company into more buildings with that company.
Use guest proof to sell. Work with operations to collect reviews, case studies, and financial results. Use them in every deal.
Keep the CRM accurate. Record every contact, stage, and next step. Run a weekly pipeline review with the CEO. For each deal, show the current stage, the next action, and your requests.
Feed the business. Tell the CEO and operations what buyers ask for and why deals stall or fail.
4. Requirements (must have)
Experience
6 or more years in business development, sales, or partnerships.
3 or more years selling to multifamily or commercial real estate decision-makers. Examples are property management companies, asset managers, REITs, or building owners.
Experience with long B2B sales cycles that have many people in each decision.
You closed several six-figure or multi-year agreements with many stakeholders. Single-call deals are not sufficient.
Proof of closing
You closed deals yourself. Supporting a sales team is not sufficient.
You can show numbers: deals closed, contract value or units signed, and time to close.
Network
Relationships with multifamily decision-makers in Chicago or a similar US market are a strong plus. If you do not have them, you must show that you built them from zero in a new territory before.
Skills
You can build a financial case that an asset manager accepts.
You can lead a negotiation from first offer to signed agreement.
You use a CRM every day and keep it accurate.
Logistics
This is a full-time job.
You live in Chicago or you can move there.
You must meet buyers in person and tour buildings on a regular schedule.
5. Traits and behaviors
You are a closer. You ask for the signature.
You see the building decision-maker as the main customer. You see the guest as the proof.
You build trust over months. You follow up without a reminder.
You work from a scoreboard. You know your pipeline numbers each week.
You are comfortable with direct feedback and direct answers.
You bring options with clear tradeoffs, not only problems.
You write clearly and simply. You do not use buzzwords.
You are hands-on. You do the work yourself. You do not need a large team.
6. Structure and reporting
Type: Full-time, exempt.
Reports to: CEO.
Location: Chicago, hybrid. You spend most weeks in the field with buyers and at buildings.
Budget: You get a separate budget for events, travel, sales tools, and sales materials. You set it with the CEO.
Support: A small team helps you with deck design, data pulls, and light marketing assets. You own the strategy, the targeting, and every sales conversation.
7. Path and promise
You can become VP Business Development as we grow into new markets. To get this role, you must meet your targets for 2 or more quarters in a row.
You build the business development playbook for a hospitality brand that leads its category.
You take over deal closing from the CEO. Your work connects directly to signed buildings and the value of the company.
8. How to apply
Apply with the form below. Include:
Your CV or LinkedIn profile.
3 to 5 deals that you closed yourself. For each deal, tell us: the buyer type, the deal size in units or contract value, and the time from first meeting to signature.
A short list of the types of companies and roles in your network. For example: property management companies, regional managers, asset managers, or owners. You do not need to give names.
We will invite the best candidates to a live conversation with the CEO.
Why Pentice
If you want to own a number, move fast, and build with AI instead of around it, this is the place. Small team, real leverage, high standards, and the people who build the systems get to run them as we scale city by city. If you want a comfortable seat where effort counts more than outcomes, we are not it.
Equal opportunity
Pentice and its operating entities do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.
Head of Sales Development Jobs by Experience Level
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Who's Hiring
Top Industries Hiring
- Banking & Financial Services
- Biotechnology & Pharmaceuticals
- Manufacturing
- Consumer Goods
- Science & Research
What Employers Look For
The qualifications that appear most often in head of sales development jobs.
- Five or more years of experience managing SDR or BDR teams in a B2B environment
- Demonstrated ability to build and scale outbound sales development programs from early stages
- Proficiency with CRM platforms and sales engagement tools such as Salesforce and outreach automation software
- Experience designing and running SDR hiring, onboarding, and ongoing coaching programs
- Strong analytical skills with the ability to report on pipeline metrics and forecast team performance
- Bachelor's degree in business, marketing, communications, or a related field
Tips for Your Head of Sales Development Job Search
Quantify your pipeline and ramp metrics
Hiring managers want to see the numbers behind your leadership. On your resume, include SDR team size, quota attainment percentages, and how quickly you ramped new hires to full productivity. Vague statements about building teams get screened out fast.
Highlight your outbound methodology by name
Heads of sales development are hired to install a repeatable outbound motion. Name the specific frameworks you have implemented, whether that is a cadence structure, a cold-call playbook, or a territory segmentation model. Generic leadership language will not stand out.
Apply early to roles that fit
Migrate Mate lists head of sales development openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Target companies at the right growth stage
A series B startup needs someone who can build the SDR function from scratch, while a Series D or public company needs someone to scale and optimize what already exists. Filter your search accordingly and tailor your resume to match the stage the company is actually in.
Prepare a data story for the first interview
Expect the first call to focus almost entirely on your pipeline numbers and hiring decisions. Know your best and worst quarters, what caused each, and what you changed. Interviewers for this role probe for self-awareness and analytical rigor, not just results.
Negotiate comp structure before accepting
Head of sales development compensation often mixes base, bonus tied to pipeline metrics, and sometimes equity. Before accepting an offer, clarify exactly how the variable component is calculated and whether it is based on meetings booked, opportunities created, or revenue sourced.
Head of Sales Development Jobs: Frequently Asked Questions
Which companies are hiring the most head of sales developments?
The companies hiring the most head of sales developments right now include Apple, MAERSK, and Pulley, with the largest share of openings in New York, California, and Texas, based on current listings on Migrate Mate as of November 2026. SaaS and enterprise software companies consistently account for the largest volume of these roles.
How many head of sales development jobs are remote?
About 78% of head of sales development openings are fully remote or hybrid as of November 2026, reflecting broad acceptance of distributed leadership across the sales function. Roles focused on strategy, coaching, and pipeline reporting tend to be the most remote-friendly, while positions tied to in-person sales culture or office-based SDR teams are more likely to require on-site presence.
How do you become a head of sales development?
Most heads of sales development start as individual SDR contributors, move into a team lead or senior SDR role, and then step into an SDR manager position before reaching the head level. Building a record of improving SDR ramp times, quota attainment, and pipeline quality at each stage is what creates the progression. Developing expertise in outbound methodology, hiring, and performance reporting accelerates the path significantly.
Can you get hired as a head of sales development without direct management experience?
It is possible if you have led informal team structures such as mentoring junior SDRs, running enablement programs, or owning a territory playbook that others followed. Employers hiring for a first-time build-out are sometimes open to candidates who have not held a formal management title if they can demonstrate deep outbound expertise and clear thinking about how to structure and coach a team.
What does the head of sales development interview process look like?
The process typically starts with a recruiter screen focused on your background and leadership philosophy, followed by a hiring manager interview that goes deep on your pipeline metrics and team-building decisions. Later rounds often include a presentation where you outline a hypothetical or real SDR program build-out, and final conversations with a VP of Sales or CRO who evaluates strategic fit and cross-functional alignment.
Where can I find and apply to head of sales development jobs?
You can find and apply to head of sales development jobs on Migrate Mate, which lists current openings from across the United States. Find roles that match your experience and apply directly to each listing.
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