After OpenPhone raised $14 million in Series A funding, I joined the team as Head of Sales, tasked with building the revenue team.
Before I joined OpenPhone, we didn’t have a defined go-to-market sales motion. The company had found product-market fit, but we needed to establish the sales engine that would allow us to grow at scale.
Personally, I like to think of developing a revenue engine in the same way I do cooking. Before you worry about the quality of the ingredients, you need to build out a recipe. If you haven’t nailed the fundamental science of cooking and laid out formulaic steps, then even the best ingredients won’t save your meal.
And yet, when it comes to cooking up an efficient sales engine, it’s not easy to find a straightforward recipe. Founders may give each other advice on Reddit or in Slack groups, but very few will truly talk tactics that scale.
I want to change all that. After growing Pinterest’s SMB sales team, I’m now building out OpenPhone’s Revenue team. Putting the right systems in place will give our team the foundation to scale — both this year and all the way through to an IPO. I’d like to lean on my experiences and help others as they solve similar problems.
Every step in our recipe for success is designed to be scalable, repeatable, and efficient.
If you want to build out a streamlined sales team that enables you to lead your team well beyond Series A, read on. We’re sharing the exact 5-step recipe we’re using to scale.
1. Plot out the customer journey
Every company is different, so breaking down what happens in your funnel is key to identifying your challenges and opportunities. Here’s how we did this for OpenPhone.
Understand how customers enter the funnel
At OpenPhone, thousands of new customers enter our ecosystem each month. These mainly come from two sources:
- Product leads – It’s free to sign up for a trial of OpenPhone, so many of our customers join this way, eventually becoming paying customers after the trial period.
- Talking to sales (by completing a web form) – Some customers reach out to our Sales team before signing up, so we’re in touch with them from the very beginning.
This data helps us understand who our sales team should talk to and when. On any team, time is a finite resource, so it’s important to take informed bets to prioritize which prospects to reach out to.
Identify friction points
A friction point is any step in the customer journey where a lead decides they won’t purchase your product. You need to develop a sales assist motion to reach out to these individuals in the short term. Over time, you should work with Product and Engineering to resolve these friction points within the product itself.
We identified a few friction points within the sales journey at OpenPhone, including the fact that 50% of users who started a free trial converted into paying customers (we knew we could get that rate even higher).
Analyze the data to discover more about your customers
While knowing your friction points will tell you where the holes in your funnel are, you’ll still need more data to learn how to increase your conversions.
During an audit, we looked at:
- What was the overall composition of our leads?
- What type of prospects were converting to paying customers?
- Where were prospects leaving the funnel if they didn’t convert?
- What kinds of actions were users who turned into paying customers taking?
This gave us the type of data we needed to start designing sales motions to increase customer conversion rates.
2. Activate a sales motion based on low-hanging fruit
There will always be four to five areas you can focus the team on within a product-led growth (PLG) motion. Since we’re a small team, we have to take bets and focus on the lowest-hanging fruit.
In our case, one clear friction point we needed to tackle was the 50% drop-off we saw after the users’ trial period ended.
Removing friction from the trial process
We decided we needed to have reps actively reaching out to users during their trials. To help our sales reps prioritize their outreach, we started scoring prospects based on the actions they took, such as:
- Inviting their team to use OpenPhone
- Sending messages within the platform
- Using our integrations with other tools
We also use third-party data that shows company size to help us prioritize outreach.
With this motion in place, as soon as a lead reaches a certain score, they receive a personalized email from our Product Specialist, who manages our product-qualified leads. We took the time to automate this outreach using two different systems. It’s critical for us to always delight potential customers, though, so we were intentional about having all automated emails come from our actual team members.
With our automated emails, we are always iterating on our messaging using A/B tests and we focus on sending clear, concise, non-spammy, and non-salesy messages.
Our new sales motion led to two important results.
First, we had automated our Product Specialist’s upfront work — meaning they could now spend their time having conversations with qualified leads rather than spending a third of their day manually emailing prospects.
Second, our targeted outreach allowed us to get in front of higher intent customers quicker, helping them get more value out of OpenPhone and turning them into paying customers.
And it worked. We drove a 20% increase in customer conversion rates and a 140% ACV increase when we removed friction from the trial process. This single shift has turned into a six-figure incremental gain in annual recurring revenue for the company.
Streamlining responses to sales inquiries
Another low-hanging opportunity was sales inquiries that came in through our web form. When I joined OpenPhone, they solely came in as notifications that landed in our Slack channel.
A sales rep would then pick opportunities up randomly from the channel and follow up individually but didn’t enter prospect data into a Customer Relationship Management (CRM) system Leads were slipping through the cracks, and it took team members about four minutes to reach out and log activity for each inbound lead.
This was a clear friction point and gave us an opportunity to create a scalable process. We automated the data flow and outreach for our sales inquiries, freeing up our team’s time to chat directly with qualified leads.
3. Select tools to scale your team’s efforts
Although we’re a Series B company, we still have a relatively small sales team.
Every tool we invest in needs to help our team be more efficient. Before we buy something for our sales tech stack, we run it through a pros and cons list based on the following factors:
- Usability. When looking for tools, I treat our sales reps as my customers. They need to actually use it and see the value in it, or else we’re throwing our money away.
- Scalability and workflow fit. Does a new solution work with the tools we’re already using?
- Time to deploy. How long will it be until the team can start using it? How long will it take engineers to set up?
- The amount we’ll pay. What will we be paying for the tool every year? Are competing tools a better deal for the value?
- Resources post-sales. Does the tool have a solid support team we can reach out to if we run into issues after subscribing? Internally, do we have a team member who can continue to own the tool post-deployment?
When it’s time to buy, we also need to weigh whether a con trumps a pro. For example, if a tool is expensive but has excellent ROI potential and post-sales support and productivity benefits, we’ll probably buy it.
The tools that should make every startup’s sales tech stack
Every company’s needs are different, but there are a few tools that every sales rep should have access to. Here’s what I’d recommend and what we currently use at OpenPhone.
Most startups will use a less expensive or free CRM like HubSpot.
We invested early into Salesforce. It does everything we need a CRM to do: our email and selling tools are all integrated with Salesforce to make our sales team’s lives easier.
I knew from my time at Pinterest that a CRM becomes the most crucial tool in your toolkit when the sales team starts growing. Switching from a more affordable CRM with fewer features to a more advanced one like Salesforce that can actually scale when we hit Series B or C would’ve been a nightmare — it’s a six-month job.
For this tool choice, implementation considerations trumped cost.
Engagement and automation
We use Outreach to automate a ton of our emails through customized email sequences. It plugs into Salesforce, so we can see all past communication in our CRM. It also breaks down daily tasks (such as emailing certain leads or following up with others) so reps know exactly what they need to do each day.
Outreach was a more expensive solution than other engagement software options out there, but it was super easy to deploy. We also love the Outreach trigger feature set, which automates emails based on certain Salesforce criteria. For us, that made it the right decision.
We use Apollo to help us find prospects’ email addresses.
In my experience, Apollo is the best prospecting tool on the market, hands down. Not only is it affordable, but it’s easy to integrate with both Salesforce and Outreach, making it seamless for reps to add prospects into their streamlined workflows.
Revenue intelligence & call recording
A revenue intelligence tool like Gong lets you pull more data from sales reps’ calls. Gong gives me incredible leverage to coach my team. I can review calls weekly and give the team feedback, all without having to join live calls.
Another huge benefit of Gong is that it allows for scalable qualitative analysis. For instance, I’ve created trackers to share customers’ frequent feature requests with our product team. I also create trackers to analyze coaching opportunities — we’ve found when we intentionally discuss specific pricing details on calls, we close 75% of deals. When we don’t, only 45% of our deals close.
There are cheaper solutions, but Gong is easy to deploy and has great post-sales support.
We use Pocus as our main lead scoring tool. It grades every prospect entering our pipeline and feeds the data into Salesforce and Outreach.
We considered using other lead-scoring and account health-scoring tools, but we found them to be super complicated. Also, their time to integrate was months rather than weeks. We would’ve had to redesign our sales playbooks and Salesforce architecture to make them work, and our RevOps Manager would have had to spend hours overhauling existing systems.
In this case, deployment speed and integrations won out over other considerations and trumped the design considerations of other solutions. We simply went through a series of brainstorming sessions with our Pocus team and handed them the keys to run the integration.
With the integration, each new trial gets a lead score appended into Salesforce, and we run automatic sales motions based on particular criteria.
For our appointment scheduling tool, we opted for Calendly. We weighed more robust scheduling solutions but couldn’t justify paying six times more for them. Calendly is working great for us.
While Salesforce is a robust tool, it doesn’t always do what you want it to. So we use Scratchpad, a tool that layers on top of Salesforce, saving our team hours every day. It optimizes workflows for reps and updates opportunities inside Salesforce automatically.
For instance, we generally need to bulk-update records in Salesforce a few times a week — a process that used to take at least an hour in Salesforce. The ease with which this can be done in Scratchpad makes our lives easier.
Calling & texting
Our sales and success teams use OpenPhone to stay in touch and build our customer relationships. Why I love using OpenPhone for sales and success comes down to four fundamental aspects:
- All our conversations are recorded.
- We collaborate across shared phone number inboxes.
- CRM logging – we route all SMS + phone activity into our CRM, which allows for reporting and analytics.
- Business continuity – if a rep is out of town, we never miss a beat as we can add other team members to that line.
Rep performance analytics
We want to provide our front-line managers and reps with tools that proactively surface data and insights that help them get ahead of risks to hitting quota. Salesforce is candidly terrible at predictive indicators. For this, we chose Atrium, which scrapes Salesforce and Gmail data to surface leading indicator trends to ensure our team is always in a position to exceed quota.
These leading indicators are then pushed via Slack to our reps at the beginning of each week, so they know where to focus their efforts.
The total cost
I know you want to know numbers, so here they are.
Our total tooling spend is about $82K a year for our current team of eight (revenue operations, CSM, and sales).
Here are three reasons why we landed at this total amount.
1. Buying decisions are based on where the company is going — not where we’re at now
Building a sales team is an investment in the future. Investing in our tech stack is allowing us to springboard revenue by simply being more efficient. As a result, we’re looking at triple-digit quarter-over-quarter growth!
We’ve purposely invested in systems over people to ensure we’re designing for scale. At the end of the day, building a platform — and then incrementally adding sales reps — will win every time. I’ve learned the hard way that you shouldn’t plan to double, triple, or quadruple your sales organization unless you have the operations in place to scale that growth.
2. We don’t default to the cheapest tool
Our largest line item is Salesforce, at roughly $24,000 per year. Salesforce is undoubtedly expensive, but it’s also powerful. Our CRM will scale with us as we grow, so we won’t need to move to another solution in the future.
Bottom line: if we find value in a tool from a production and productivity standpoint and it’s helping us hit targets, then we invest.
3. We’ve really thought about how we invest in deployment
Most people assume that the moment you deploy Salesforce, you need to hire a Salesforce developer. Salesforce is notoriously clunky and mysterious to use, which is a big drawback to the tool. However, we’re not at the size yet where we need to invest in a full-time Salesforce developer — so we chose to outsource development. Why? Not only does this move save us money, but many senior Salesforce developers tend to be a few steps removed from the frontline. Instead, we have a RevOps hire that’s a fast-moving problem solver to help grow with the organization and build with us.
Salesforce workflows set up through Swantide
Our RevOps Manager also worked directly with Swantide, a Salesforce setup, and management agency, on Salesforce deployment for our team. They provide a tremendous amount of value, offering us dedicated customer success support and tools to automate workflows. They’ve brought us the expertise — and saved us a ton of money by not having to hire an in-house a Salesforce engineer.
Aside from managing our tech costs, we’ve also set key performance indicators (KPIs) for our team that help us more accurately predict our revenue.
4. Track KPIs that measure inputs, not outputs
A lot of sales leaders will manage to outcomes — which, in a sales organization, is usually just revenue. As sales leaders, when revenue is good or bad, we need to understand why. Even more critically, we need to know if things aren’t going well long before they get bad.
While, of course, an organization needs to have revenue goals as their north star, managing to revenue is too little too late. If you manage to outcomes, you can only tell that something has gone wrong when a target isn’t reached.
By managing to inputs, you can ensure the actions your team takes today will pay off tomorrow. This book fundamentally changed the way I lead teams.
For example, at OpenPhone, it generally takes us 12 days to close a deal — so I know if a rep doesn’t make any calls today, their revenue won’t look healthy in two weeks’ time. We can more accurately predict the long-term health of our business by setting KPIs that outline the daily actions reps should take.
When presenting this approach to reps, it’s all about empowering them to hit their goals. They can understand exactly what it takes to be successful by understanding which inputs are needed.
Personalize KPIs to your teams’ sales motions
Depending on which area of the business team members own, they’ll likely need to use different tactics to meet their goals. A Customer Success Manager in charge of expansion deals, for instance, will likely need to take a different approach than a Business Development Rep. Set different KPIs for each.
When it comes to the sales assist motion, our key outcome is to bring in incremental revenue in the form of net new teams. But the KPIs we set for this motion aren’t focused on landing X new teams per month. Instead, KPIs are based on:
- How many emails reps are sending
- How many meetings they’re having
- How many new opportunities they’re creating
Managing to inputs rather than outcomes gives me the predictive indicators I need to make sure we’re running a very healthy business. And when things aren’t going to plan, we can easily diagnose the gaps in our business.
5. Assemble a team
Last but not least, it’s time to build a team that can deliver — which is all about hiring carefully, onboarding thoroughly, and making sure your team has the resources they need to succeed.
Develop a hiring profile
Often, I’ll see startups simply hire sales reps and throw them at a revenue goal. However, that usually won’t get you the targeted results you need. Instead, hire reps that will tackle specific sales motions.
When building out a job description and the hiring process for a specific role, you’ll need a clear understanding of the problems you want this employee to solve. Then, work backwards to define your ideal candidate profile. Don’t hire for experience — hire for the role. I’ll hire people with zero prior SaaS experience all day, every day if the role suits a candidate. My last few hires were former accountants, real estate CSMs, and sales recruiters.
For our sales assist motion, we decided to bring in a new sales rep. We needed someone with the technical chops to run 50 calls a week while also being analytical enough to help us build out the sales assist motion.
We ended up hiring a former accountant since their financial consulting skills perfectly fit the role.
While we always hire candidates who are humble, analytical, and natural problem-solvers, we make sure we hire a person who is specifically suited to the role we’re building.
Create an onboarding process that scales
Playbooks are why OpenPhone will have no problems scaling our sales team when we’re ready.
We’re designing our playbooks to allow a friction-free onboarding experience for our teams. Since we’re a fully remote company, we want to be super aware of the mechanics of bringing on new team members. (Let’s be honest: starting a job at a new company can be isolating if we don’t solve for collaboration.)
Here are a few things cemented in our onboarding flow:
- Who we are and what our philosophy is at OpenPhone
- Meeting the team — both the sales team and the wider OpenPhone team — to get to know each other as humans and forge genuine relationships
- Our expectations for their first 90 days
During the onboarding process, we also have a manager check on them every other day and pair them with a ramped peer.
All our playbooks include:
- Checkboxes to complete. Each playbook has a menu and a quick welcome to the team. From there, sales reps onboard themselves to the role by exploring our playbooks, which detail every aspect of our sales operation. (If a new rep comes in and is a Salesforce rookie, we’ve created an entire playbook that walks them through how information moves from databases into the CRM.)
- Engaging tasks. New reps have tasks and quizzes to complete for each playbook to make onboarding more interactive.
- Weekly expectations (in playbooks for our fully ramped team members). Based on modeling, every sales rep knows exactly what they need to do and what their goals are. For instance, for our sales team, we usually expect reps to have 70 new leads, 30 new customer meetings, and 20 new opportunities each week. There’s also a framework for reps to follow when a lead enters their sales funnel and step-by-step documents on what to do next (e.g. what tools and sequences to use).
Bringing in a competitive or interactive aspect can help make the lessons in our playbooks stick. Here’s our revenue team playing a game of Competitor Jeopardy:
Everything in our sales playbook has a purpose, with the goal of allowing reps to train and troubleshoot problems on their own.
We built for velocity so we can scale the team effectively
If OpenPhone’s founders came to me today and told me the company was hiring 100 more sales reps so we can expand into new markets/segments by the end of the quarter, I would say, “No sweat.”
We’ve invested in our sales tech stack early and spent time documenting playbooks. If tomorrow we needed to 20X our sales team, we have the scalable, repeatable, and efficient mechanics in place to manage that aggressive growth.
We didn’t just buy sales tools because we thought our team needed them. We invested in a sales tech stack that makes our team productive and benefits our customers.
Our processes, tools, and playbooks are all aligned, and they’ll support stronger year-over-year growth, which allows us to focus on running a profitable business unit.
I’m biased but bullish that these are the fundamental basics for standing up a revenue organization. This is how every sales engine should be built — on a solid foundation that allows you to scale. Have any questions after reading this? Reach out to me directly at [email protected].