How to Build a Billion Dollar Outbound Sales Team w/Carrie Bosworth (SVP Sales, Checkr)
- It took us 6-9 months to get outbound ready with the right books [of accounts], the right reps, the right leaders, and the right motions.
- Everybody in the organization should be outbound all the time.
- While your c-suite must be eager to drive outbound, they don’t typically have the time to write messages. So, draft a short note on behalf that covers (a) your exec’s background (b) CTA for a 15 min call to learn more and explore ways we can help.
- Leverage your Board for outbound.
Community-Led Growth w/ Andrew Ettinger (CRO, Appen)
- Developers don’t have a ton of respect for salespeople. You sell by adding technical value not by running traditional qualification and discovery.
- Developers don’t have money and they don’t know how software gets procured in their organizations. There is a delicate dance to get them to take you to their VP of Engineering. To earn that right, set the expectation up-front that you will run a deployment workshop for them in exchange for a meeting with their boss assuming the developer sees value.
- Engineers are not salespeople. When they talk about your product to their boss, they will talk about how your tool benefits them not the VP of Engineering.
- Any time you are in open source, your first job is the community. Focus on 3Cs
- Community: solid technical contributions to the core open-source code base
- Content: Rich documentation, certifications, etc. that are ungated
- Conversion
- Open-source software companies need Developer Advocates whose sole job is to help the community. They may report into Product or Marketing but typically not Sales.
- AI will increase the need for technical sales support (sales engineering) since prospects are trying to understand if solutions are technically feasible and secure. – Roberge
How to Scale a Billion Dollar Sales Team w/ John McMahon (Board Member, Snowfalke)
- Add incremental sales capacity based on incremental (segment/geo) opportunity rather than optimizing for complete coverage.
- If you have to choose, hire for sales expertise with a given motion (ex: enterprise SaaS) rather than industry expertise. With intelligence, drive, and coachability, they will pick up product and industry knowledge pretty quickly.
- I spend the first 30-45 minutes of an interview asking the candidate about their character. I want to know how driven they are. What is the toughest situation you have ever been in? What is the most competitive situation you have ever been in?
- Your capacity model should include: target total bookings, ramp time until hitting full quota, ramped productivity, and attrition. Figure out how many reps you need to hire and when you need to hire them. As a starting point for enterprise, assume a 6 month ramp, $800K/yr ramped productivity, and 25% attrition.
- Average attrition in sales is 45%. – Roberge
- Early on, start with a 5:1 rep-to-manager ratio (in enterprise) so managers have capacity to recruit, hire, train, and manage their team.
- For inside sales, the rep-to-manager span of control is typically 6-to-8:1.
- Zero attrition is bad since everybody makes mistakes when hiring people.
- Understand why you lost a rep – whether they quit or were terminated. You either hired the wrong person, you failed to train them, or you could not lead, coach, & develop them. Share your learnings with the rest of the organization on what went wrong.
- If you can’t get your differentiators into the decision criteria of the proof of value, then you are going to lose.
- Only three people can control a deal: you, your competitor, or the prospect. The longer the sales process goes on, the more great reps take control.
- It is a red flag if your champion does not know who the competition’s champion is.
- Often the reason you win the deal is not because you have the best product, it is because you have the best champion. – Roberge
- A true champion must be willing and able to go to bat for you. The able part is the most important since people will seem/be willing. – Roberge
- The ultimate test of a champion is if they can get you a meeting with the economic buyer.
The Untold Story of Scaling HubSpot’s Sales Team w/ Brian Halligan (co-founder, HubSpot)
- When hiring a rep, ask yourself, “Would I buy from this person?”
- I learned sales and sales leadership by meeting with my mentor John McMahon 4 hours per month and via quarterly dinners with peers. – Roberge
- Even if you intend to eventually sell through channel, go direct at the start to figure out the go-to-market motion. – Roberge
How to Move from Founder Selling to Scaling a Sales Team w/Jonathan Anguelov (co-founder, Aircall)
- Personalize based on facts you gather when you are verifying the need for your solution.
- Make 30 precise calls rather than 300 random calls.
- Jonathan continued to sell until the company reached $60K MRR ($720K ARR)
- If there were a universal playbook, then every SaaS company would reach $1B ARR. But, every company company is different, every product is different, every demo is different.
- When reviewing a call recording, have the rep who made the call self-assess rather than having others comment.
- Don’t just forecast the quarter, forecast week 1, week 2, …, week 40.
The Funnel and Revenue Math w/ Matt Plank (CRO, Rippling)
- Get sales capacity to match demand generation capacity – Roberge
- In a new market, you typically need to start with a lower OTE:quota mulitplier.
- Stay on monthly quotas as long as you can.
OpenAI: Why They Had to Un-do Sales with Aliisa Rosenthal (Head of Sales, OpenAI)
- With usage-based products that require sales (security reviews, legal redlines, etc.) and service involvement, set committed consumption minimums to identify real buyers and to ensure efficient growth.
- As hard as it is to say no, only work with customers that you expect will be successful with your solution. (Roberge)
- In an AI-driven world, AEs focus exclusively on human-to-human interaction and AI takes care of all the mundane tasks from research to CRM updating to email follow up.
Unraveling the PLG Trap w/ Oliver Jay (Founding CRO, Asana)
- As an early stage head of sales, your job is not only to sell but also to build the company by partnering with the technical side of the business.
- Live by leading indicators, esp. pipe generation relative to your sales cycle.
How to Take Your Sales Playbook Upstream w/ Kevin Egan (Head of Global Enterprise Sales, Atlassian)
- To land an Enterprise business unit, you need a precise use case that you facilitate better than anyone else can – faster, better, and easier to use.
- When interviewing enterprise sales rep candidate, ask them to tell you about a big win they are most proud of. You are looking for them to describe:
- Who were the stakeholders?
- Where did things get difficult? What did you have to do to overcome the challenge?
- Were they in the driver’s seat?
- One way to avoid channel conflict is to pay the rep the same whether the deal is sold direct or with a partner.
- Questions enterprise customers ask that signal is it is time to go upstream. We could go bigger if…
- … you negotiate legal terms for us
- … you provide more favorable pricing for large numbers of users
- … you were to put data centers in specific countries/regions
- When you go up-market, you are basically starting over. You need renaissance reps who can capture the voice of the customer and bring it back to leadership.
Don’t Lead with The Product, Lead To the Product w/ Doug Adamic (CRO, Brex)
- Figure out what your customers will need as they grow and move upmarket
- The primary skill one must develop to move from a transactional to a strategic rep is business acumen centric discovery – the ability to converse with the prospect about the business they are in and the job they are performing.
- People buy because (1) they are already in trouble, (2) they see trouble coming, or (3) they want to be a hero.
- Don’t lead WITH your product, lead your prospect TO your product.
How to Build a Moat Strategy That Wins w/ Stevie Case (CRO, Vanta)
- In many cases, strong execution is the only real moat you can build.
- Ask yourself: Imagine 10 engineers quit Google and got $10M from a Tier 1 VC. Why would you still win? – Roberge
- Customers should care that you have a multi-year lead but they won’t unless you explain to them why it matters. Beyond features, this is often your knowledge of how customers evolve and derive value from your solution over time.
- Deal inspection questions:
- What gives you confidence they are going to sign this week? What does this unlock that is meaningful to their business?
- Who are the (other) stakeholders involved in the decision?
- Why might they not sign?
How to Create Customer Advocates In Your Go-To-Market w/ Jay LeBoeuf (Head of Sales, Descript)
- Soften the beach by showing off your product to your prospect’s procurement person.
- Companies don’t have relationships with each other – individual within the companies have relationships. If a person leaves on either side, you need to rebuild, often from scratch.
- Product usage is more complete and accurate compared with NPS data. – Roberge
- Don’t put reps on a commission plan until you have product-market fit. – Roberge
How to Add a Sales Org to Your PLG Company w/ Dino DiMarino
- Inbound centric companies should experiment early to build an outbound prospecting muscle since you will eventually need it.
- Reps who are able to hit quota on converting inbound will chose the path of least resistance and ignore outbound SDR-sourced leads. In this instance, you’ll need pure outbound reps. – Roberge
- Enterprise reps must be great at: (1) understanding the political dynamics of the organizations they sell to and (2) how they develop champions. – Roberge
- In a complex deal, you should have both a business champion and a technical champion.
How to Align Your Sales and Marketing w/ Mike Weir (CRO, G2)
- Measure the unit economics of each channel – marketing sourced pipeline, AE sourced pipeline, and SDR sourced pipeline. – Roberge
- Get away from a culture of credit. If you emphasize AE sourced pipeline, don’t be surprised when marketing- and SDR-sourced leads languish.
How to Integrate Your First Sales Hire w/ Kyle Parrish (VP of Sales, Figma)
- Monitor WAU (weekly active user) retention
- Exceptional customer support is critical when entering a new market segment
- While sales acumen is more important, early sales hires should have deep technical expertise in your product; they are pseudo-sales engineers who can sell.