With six startup and two big company enterprise software experiences, Mark has repeatedly driven revenue results with prescribed process and tempo.
Startups introduce unique challenges to revenue growth, where reliance on delegation to traditional sales roles (e.g., garden variety account executives, sales engineers, sales development representatives and first-line managers with average talent, are order takers and lack creativity and presence) are incongruent with customers' needs and expectations.
What is needed is a playbook - a living document on demand generation, pitch deck, qualification questions, effective demonstration and trial criteria, pricing, beneficial customer success and more. Not to be confused with later-stage, big-company playbooks meant to help average talent succeed and scale revenue.
First-time or technical founders and even venture capitalists may misdiagnose revenue growth requirements - where product market fit, brand awareness, and product maturity are missing - with traditional sales leadership and process that only work at companies with product market fit and dominant products.
Mark's unique value
I've read if you ask professional athletes why they are great at something, they may highlight a valid point or make things up, since they cannot objectively know why they are great. In that vein, here's feedback that I've received from superiors, customers, and peers about why I am excellent at revenue growth:
Mark's focus areas
Co-founders and leadership are welcome to email if interested in leveraging Mark's sales expertise from doing a healthcheck of an existing sales org or designing process, tools and building a new sales org.
The following are Mark's observations, considerations, and recommendations for early-stage startup revenue growth:
The bare minimum to get started
Sales porn
The point is you know it when you see it. Watch out for revenue leaders who do any of the following:
Playing office
Playing office is members of a revenue org looking busy but not moving the needle. At first glance, probably with some self-promotion, it appears like something good is there, but it's not. Watch out for revenue leaders and members who do any of the following:
Hiring & Recruiting
In early-stage startups, account executives and sales engineers are often referrals from leadership or in-bound candidates willing to take the risk of joining a startup.
Filling a pool of candidates is not the hard part; many account executives and sales engineers are constantly looking for new opportunity. It is much more difficult to screen for the right fit for a startup.
Candidates should be quick studies, who are bright, clever, and curious. They should be able to learn the product quickly, and they should be able to present the product effectively to customers.
Prior performance is not a guarantee of future success. Back channel candidates and their companies. Success at a larger company with a dominant product may not translate to success at a startup.
If a revenue leader wants to quickly hirer from their network with little screening from other leadership and the broader company, you risk creating a situation where people are hired for loyalty and not for their ability to contribute to revenue. The proverbial "You scratch my back and I'll scratch yours." This human behavior can be toxic.
Also look out for revenue leaders who have strict guidelines for new hires they do not know but don't follow that scrutiny for their network.
Order takers
In a startup, order takers fulfill inbound leads that were highly qualified and unless you muff it up, were going to close anyway. Watch out for the account executive taking credit and playing up these closed deals, which is done in part due to ego but also to deflect potential lack of success in closing difficult opportunities or finding organic opportunities on their own.
It's important to note that if a startup only has order takers, your probability of substantially growing revenue is low unless a firehose of qualified inbound leads are coming in. Lack of leads is typical of early stage startups so order takers really are not welcome or helpful.
Be mindful of account executives closing deals that were really order-taker-like. In other words, watch out for the following:
Territories
I do not recommend geographic territory assignment for account executives in early-stage startups if enterprise is the target customer. Fortune 500 companies heavy-weight to specific regions like New York yet have distributed decision makers. Second, geographic territories create a single point of failure. You're best to distribute a target account vertical e.g., financial services, across all of your account executives for highest probability of closing revenue.
Sales development representatives on the other hand can be geography-based to assist all of the account executives.
If the target market is SMB or mid-market, then geographic territories are fine.
Once you attain solid product market fit and have won significant, repeatable business, geographic territories make sense.
Over time though you may want to have industry-specific account executives if your product is specific to an industry and for the account executive to be credible with customers.
Then also have geography-based account executives for the bulk of your target cutomer base.
Sales org structure
In startups, some of the best talent to drive early revenue are the co-founders, founding members, and the first couple of sales staff.
From the customer point of view, customers value startups because of the knowledge and expertise that the startup brings to bear in every conversation.
This experience desired by customers is rarely achieved with traditional sales org structures seen in mid to large compaines where there is massive product market fit or the product is dominant and can basically sell itself.
Conversely, startups do need to put in place building blocks to free up co-founders and key sellers to focus on high-value opportunities and building out the product. This involves building the first account executives, sales engineers, sales development representatives and if the business model necessitates it, a partner manager.
Hiring and filling seats are the easy part, but leadership will be sorely disappointed if there isn't: Without one or all of these, the quick revenue org buildout results in a reduction in force and confusion in the startup's strategy.
Sales and revenue attainment is about at bats so even Series A and B startups should invest in hiring 1-4 account executives, 1-2 sales development representatives, and 1-2 sales engineers for coverage.
When to do these initial hires is a function of the product, the market, and the competition. If the product is not ready, the market is not defined, then the hires should be delayed or reduced, relying on the initial sales leader and co-founders to do the bulk of sales.
Onboarding and enablement
Onboarding is the process of getting new salespeople up to speed on the product, the sales process, and the tools they need to be successful.
Be wary of the revenue leader who over-engineers the onboarding and training process. In startups, the product is changing rapidly, so a frequently asked questions is a good start which will be a living document for account executives and sales development representatives to use as a playbook during calls.
A good onboarding process should include a mix of classroom training, shadowing, and hands-on experience. The goal is to get the new salesperson comfortable with the product, the sales process, and the tools they need to be successful.
Use products like Chorus or Gong to record calls and provide feedback to new salespeople.
During the interview process, put extra effort in screening for candidates who are bright, curious and quick studies.
Account executives, sales development representatives, and sales engineers who complain that there is not enough training are not the right fit for a startup and a red flag.
The pitch deck
The pitch deck is a critical part of the sales process. It is the first thing that a potential customer sees, and it is the first impression that they get of the product and the company.
The pitch deck should be clear, concise, and compelling. It should tell a story, and it should be easy to understand.
The pitch deck should include information about the problem, the product and how it addresses the problem, how the product is unique and differentiating from the competition, the use cases the product can be used for, the economic and business value the product produces, and the business model.
Check that the pitch deck is not too long. A good rule of thumb is to keep it to 10-12 slides or hide specific slides for specific audiences.
Do not rely entirely on the pitch deck and have the account executive or sales development representative be able to speak to the problem, value proposition and use cases without the deck. Even ask the prospect when the meeting begins if they would like to see the deck or just speak to the problem and value proposition. That will force them to listen and engage.
The pitch deck should be a living document and should be updated regularly to reflect changes in the product, the market, and the competition.
A good pitch deck should be able to stand on its own, as a document that can be sent to a potential customer, or used as a presentation in a meeting.
Be wary of the revenue or marketing leader who over-engineers the pitch deck. The pitch deck should be a tool to help the sales team sell, not a work of art.
Sales process
Startups have speed and nimbleness as advantages but sales still requires org structure and process to effectively onboard talent, communicate progress to sales leadership, co-founders and the board, and accelerate building top of funnel and closing revenue.
The mistake is to think excessive process will drive revenue and the art is implementing just enough process to accelerate revenue.
CRM hygiene review
A CRM like HubSpot or Salesforce may be in place but with sales turnover and outside consultant configuration, the lead, account, revenue opportunity and activity data may be inconsistent or worse corrupt and unusable for reporting.
A CRM hygiene review is a good first step to ensure that the data is clean and that the sales team is using the CRM effectively.
The review should include a review of the data in the CRM, a review of the sales process, and a review of the sales team's use of the CRM.
Best practices for startups are to try and leverage as much out-of-the-box functionality as possible, and to avoid customizing the CRM too much. Having said that, custom fields to track qualification and ideal customer profile metrics and reporting are a good idea.
Lead qualification
Whether inbound or outbound leads, devising a playbook to qualify is imperative to best utilize resources like account executives and sales engineers for meetings and trial support.
The playbook should include a set of questions that the sales team can ask the customer to determine if they are a good fit for the product, and if they are likely to buy.
Qualification elements range from ideal customer profile-specific to generic budget, authority, need and timeline.
Pipeline
A sales pipeline are made up of opportunities, which are potential revenue events with customers. Opportunities are created by account executives and they include information like close date, revenue amount, sales stage, forecast category, and probability of closing to help the account executive, revenue leader and startup forecast revenue.
The reality is that most opportunities will not close in a given quarter so it is important that account executives build 3-4 times more pipeline that the revenue goal a.k.a. quota.
Building the pipeline is not solely on the shoulders of the account executives, yet they does have to be organized and diligent to properly qualify leads, create and progress opportunities. Account executives also outbound prospect and produce pipeline from their own efforts.
Marketing and sales development representatives indirectly help and contribute to pipeline by producing leads for account executives to qualify and convert into opportunities for the pipeline.
Prospecting
Prospecting is the process of finding new customers for your product or service. In startups, prospecting is important because there is little to no brand awareness so the startup vis-a-vis the sales team must reach out to potential customers by way of prospecting.
Successful prospecting involves digital tools, talent (account executives and sales development representatives), the right target accounts and job titles, and measurement for accountability.
Be wary of the "spray and pray" approach to prospecting, where you send out a large number of emails or make a large number of calls without doing any research on the prospect. This approach is unlikely to be successful, and it can damage your reputation with potential customers. e.g., your email domain may be marked as spam.
Instead, screen account executives and sales development representatives carefully for evidence of an organized, thoughtful approach to to research prospects, and tailoring messaging to their specific needs and interests.
Screen former sales development representatives who are account executives to be sure they are not just "dialers" but are able to research and tailor messaging to prospects.
The best prospecting is a combination of digital tools and human touch. Digital tools can help you identify potential customers, and human touch can help you build relationships with those customers.
The key to successful prospecting is to be persistent, and to be willing to try new things. If you are not getting the results you want, try changing your approach, and see if that helps.
Do invest in digital tools but be weary of the "silver bullet" tool that promises to solve all your prospecting problems.
You need an email marketing tool like OutReach or Salesloft.
You need a contact data tool like ZoomInfo to get the right contacts at the right accounts including their email addresses and phone numbers.
You need a CRM like HubSpot or Salesforce to track your prospecting activities and results.
Sales Navigator is a great tool for researching prospects and finding the right contacts at the right accounts but keep in mind it does not provide email addresses and phone numbers and is relatively expensive.
Record calls and provide feedback to sales development representatives and account executives with tools like Chorus or Gong.
Forecasting
Predicting potential revenue is important to raising capital, hiring staff, and informing sellers, leadership and the board of directors on whether the product and go-to-market plans are achieving fit and succeeding.
The tool or CRM is not the solution but a mechanism to easily gather and share forecasts.
The art is devising a process, vocabulary and muscle to consistently forecast so that decisions at all levels can be made to impact the startup's growth.
Ask potential revenue leaders how they have forecasted in the past and what tools they have used. Get specific and have them share actual quarterly numbers and how they updated the forecast as the quarter progressed. Ask how they rolled up forecasts from account executives as well.
Salesforce has perfectly good forecasting built-in with the forecast category field on the opportunity record. You can also investigate more advanced forecasting tools that integrate with Salesforce including Clari and Mediafly.
Account Executives should update their forecasts weekly in the CRM and the revenue leader or front-line manager should review the forecast of the team weekly adding their adjustments. e.g., the leader may adjust upward or downward the team's forecast based on their experience, opinion of the Account Executive, and knowledge of the deals.
Account Executive 1:1 Meetings
Weekly interaction with the Revenue leader and account executives is important to coach, course correct and ensure proper forecasting of revenue.
Diversity of meeting agendas is important for overall revenue growth of the startup
Once a month, the meeting should focus on next quarter opportunities to prevent neglect of future revenue. It is easy to focus solely on in quarter revenue.
Another meeting, which could be twice a month, is a traditional pipeline review where the account executive reviews in-quarter deals answering quetions around budget, authority, need and timing. The Revenue leader can also recommend corrective actions in terms of whether the deal should be in quarter or a specific sales stage or forecast category.
Another meeting can focus on top-of-funnel and have the account executive share the target accounts they are focused on, their prospecting strategy and even their email templates or call scripts. The Revenue leader can also share prospecting metrics of the account executive like number of emails sent, meetings held, opportunities created.
Periodic meetings or ad-hoc meetings should also cover career growth, compensation, and overall happiness of the account executive, sales development representative or sales engineer. It is easy for a Revenue leader to overlook concerns and personal issues that their team may be experiencing and a 1:1 meeting is a great venue to discuss.
Team Meetings
Team meetings are important especially in startups where adversity and challenges can be demoralizing.
Strive for weekly but understand as the team grows these may move to bi-weekly or separate out into departmental meetings e.g., account executives, sales engineers, SDRs.
Agendas should alternate and should be defined, like in the invite.
Enablement or training is important if the product is changing frequently or if the team is growing. This should be not weekly.
Lessons learned, feedback on what's working, and what is not working are important to get the team engaged and help them feel like they are being heard and contributing. Be mindful of team members who over contribute or are showing off and be sure to engage all members of the team.
Sales engineers
Sales engineers are critical to the sales process, especially in enterprise software sales. They are the technical experts who can answer the customer's questions about the product, and who can help the customer understand how the product can meet their needs.
Sales engineers are also critical to the sales process because they can help the account executive close the deal. They can help the account executive understand the customer's needs, and they can help the account executive present the product in a way that is compelling to the customer.
However sales engineers are not a silver bullet and should not be used as a crutch for account executives who are not able to present the product effectively. Account executives should be able to present the product effectively on their own, and should only bring in the sales engineer when necessary.
When recruiting sales engineers, screen for their ability to present the product effectively, in particular their ability to give a technical demonstration of the product, and their ability to answer technical questions from the customer.
Pay attention to the type of sales engineer you are hiring. Some sales engineers come from application products and are good at presenting the product to business users. Others come from infrastructure products and are good at presenting the product to technical users. You do not want to hire the wrong type of sales engineer and in effect pay their salary to learn on the job. If the product is technical, hire a sales engineer with years of technical experience since this really cannot be learned on the job, even over years.
In a startup, the role of the sales engineer covers more areas than in a larger company. They may be asked to do product management, product marketing, and customer success work. Be sure the sales engineer is comfortable with this and has the skills to do this work else you will have an expensive resource that is not fully utilized and will have to be managed out.
Regarding compensation, sales engineers have on-target-earnings like account executives, but with a higher base salary and lower variable compensation. Variable compensation ranges from 20-30% of OTE (not base salary). In early-stage startups, criteria for variable compensation may be based MBOs as well as team revenue attainment.
Example MBOs are: number of technical demos, technical evaluations, documentation submissions, technical wins, technical renewals, support requests answered, actual closed revenue contribution, etc. What you are looking to avoid is a sales engineer who is not contributing to revenue attainment nor technically helpful, is just a "demo jockey", is not a good fit for a startup, and yet expects a percentage of revenue attainment.
Leverage job postings in states like California where technology companies post base and variable compensation for sales engineers. This will give you a good idea of what to offer and what to expect in terms of compensation.
Remember that sales engineers are one of the most expensive hires in a revenue org. Invest extra effort during recruiting to find the mix of technical and sales skills that will be most effective in your startup.
Also balance the timing of when to make the first sales engineer hire or expanding the team. If the product is very immature or changing frequently, the startup may still be required to leverage core engineering and product resources to act as sales engineers, where the sales engineer may be less effective but as expensive.
Demos
Demos are a critical part of the sales process. They are the customer's first look at the product, and they are the customer's first impression of the product and the company.
Having said that, demos, especially ones performed live, consume valuable resources like account executives and sales engineers. The best practice is to qualify the prospect before scheduling a demo.
The best practice is to have the account executive or sales development representative ask the prospect a series of questions to determine if they are a good fit for the product, and if they are likely to buy. If the prospect is not a good fit, or if they are not likely to buy, then the account executive or sales development representative should not schedule a demo.
If the product is OSS-based, be mindful not to only demonstrate the OSS features which are free. Specifically highlight the features that are paid and the value they bring to the customer.
Sales engineers should maintain a pristine demo environment. This means that the demo environment should be free of any personal files, bookmarks, or other distractions. The demo environment should be set up to show the product in the best possible light. Account executives and sales engineers should not use silly names or leave old artifacts like test1, test2, etc. in the demo environment.
If possible, account executives should be able to give demonstrations, especially if the product is not as technical. This helps build their credibility and their value to the customer.
Customers may have preconceived notions about account executives who are not able to give demonstrations. They may think that the account executive is not knowledgeable about the product, or that the account executive is not committed to helping them. This can damage the account executive's credibility, and it can make it harder for them to close the deal.
If the product is technical, then the account executive should bring in the sales engineer to give the demonstration. The sales engineer is the technical expert who can answer the customer's questions about the product, and who can help the customer understand how the product can meet their needs.
Be wary of over-engineering the demo. The demo should be a tool to help the account executive and sales engineer sell, not a work of art. The demo should be clear, concise, and compelling. It should tell a story, and it should be easy to understand.
Be prepared to hear feedback from the prospect that the demo was too long, too short, too technical, not technical enough, etc. The best practice is to ask the prospect at the end of the demo if they have any questions or if they would like to see a specific feature again.
Also be prepared for internal debate among sales engineers, account executives, sales development representatives, co-founders, leadership, product, engineering and marketing on their personal opinions of the demo. The account executive should know the customer and be able to know if the demo was effective or not. Do not waste time on internal debate.
Account executives should be aware if the sales engineer is droning on and on about technical details that are not relevant to the customer. The best practice is to have the sales engineer ask the customer if they would like to see a specific feature or if they have any questions.
Account executives should feel free to get feedback from the customer if the sales engineer's demo and responses were effective or not. Consider using another sales engineer, engineer or product manager for the next demo if the feedback is not positive.
Evaluations (Trials)
Evaluations are a critical part of the sales process. They are the customer's first hands-on experience with the product, and they are the customer's first impression of the product and the company.
Having said that, evaluations, especially ones that are not well-qualified, consume valuable resources like account executives and sales engineers. The best practice is to qualify the prospect before scheduling an evaluation.
Alternatively, if the startup is OSS-based, the best practice is to have the account executive or sales development representative ask the prospect a series of questions to determine if they are a good fit for the product, and if they are likely to buy. If the prospect is not a good fit, or if they are not likely to buy, then the account executive or sales development representative should not schedule an evaluation.
As a corporate strategy, if the product is OSS-based and the startup has good documentation and a community, the best practice is to have the prospect self-qualify and self-serve the evaluation. This will save valuable resources like account executives and sales engineers for more qualified prospects.
There's a point of view that there should be regular checkpoints during the evaluation to ensure the prospect is getting value from the product and is on track to buy. This is a good practice but be wary of committing sales engineer, engineer and product resources for these checkpoints since they clog up people's calendars and may not be necessary. Checkpoints are time commitments and should only be used for strategic or very qualified accounts with large revenue or logo usage potential.
It may be a good practice to make a running list of features to evaluate and better understand the use cases and evaluation criteria of the prospect. If the prospect is not willing to share these details, then the opportunity and the evaluation may not be qualified.
Be wary of the commitment and skill level of the prospect to evaluate the product. If the prospect is not willing to commit to the evaluation, or if they are not able to evaluate the product effectively, then the account executive should decline involvement in the evaluation or better yet ask for a check-in with the decision maker and/or economic buyer to ensure there is as qualified opportunity. The account executive should be open and clear the risks of doing an evaluation without proper skill levels and commitment.
The art of a successful evaluation is the prospect can visually deploying the product into their infrastructure. As the account executive sees this positive progression, they should in parallel reconfirm budget, who is making the final decisions, and the timeline to vendor selection and timeline to purchase. The startup has earned the right to ask these questions.
Be prepared for one or more evaluations. The initial evaluation may be quite simple, to prove that the software works as advertised. The second or additional evaluations focus on integration, customization, and the prospect's specific use cases. The account executive and startup can decide how little or how much they should be involved in these evaluations, especially if there is a simple initial one.
Partnerships/Channels
Technology partnerships, where the startup's product is integrated with another product, is the most likely initial partnership. The startup's product is integrated with the partner's product, and the two products work together to provide a solution to the customer. The partner will not resell the startup's product but if the partner's product is well-regarded, it reflects well on the startup's product.
Less common, but some startups' products are easier to setup and sell, so are good candidates for reseller channel partnerships. The partner will resell the startup's product, and the partner will provide support to the customer. This type of partnership is revenue accretive but requires more investment in training and support.
Original Equipment Manufacturer (OEM) partnerships are where the startup's product is embedded in the partner's product. The partner will resell the startup's product, and the partner will provide support to the customer. This type of partnership is revenue accretive but is very difficult to establish. I've seen popular OSS products like Kubernetes and Docker have OEM partnerships but this is rare.
Establishing technology partnerships or even strategic OEM partnerships can be performed by co-founders or leadership such as engineering or even revenue leadership. Hiring a full-time partner manager is not as necessary unless the product is partner-ready and establishing reseller partnerships is a key part of the startup's revenue strategy.
Support
In early stage startups, the product is changing frequently and in an unstable and immature state. Therefore, engineering and product resources often perform support. Like with sales engineers, be wary to over-hire technical support if they are not able to keep up with the frequency of changes of the product.
As the product matures and the startup has more customers, adding a support engineer and team structure makes sense to automate some of the work and free up engineering, sales engineering and product from support.
OSS-based startups may have a community that can provide support. The best practice is to have the startup's product be well-documented and have a community that can provide support. This will save valuable resources like engineering, sales engineering and product for more strategic work.
Customer Success
Customer success has become a popular term in the software industry. It is the process of ensuring that the customer is happy with the product, and that the customer is getting the value that they expected.
In startups, like with support, customer success may not be a good investment until the product is stable and has a good number of customers. Support, sales engineering and product may be able to handle customer success until the product matures. At the end of the day, the customer is partly selecting the startup for their expertise which tends to be in engineering, support and sales engineering. If customer success has similar expertise, then it may be a good investment.
Even in later-stage and larger companies, support may be a better function to handle customer success. The best practice is to have the support team be the customer success team with the account executive and sales engineer providing strategic support.
Compensation
Account executives, sales development representatives, and sales engineers are compensated differently in a startup. Account executives have the highest on-target-earnings (OTE), followed by sales engineers, and then sales development representatives.
Account executives have on-target-earnings that are a mix of base salary and variable compensation. The variable compensation is based on the account executive's attainment of their quota, and can range from 40-50% of OTE (not base salary).
The commission rate is specific to the account executive and calculated as the account executive's variable compensation divided by the account executive's quota.
Initially, the startup may consider using the same commission rate for new business and renewals. However, as the startup grows, the startup may consider using different commission rates for new business and renewals. The commission rate for renewals is typically lower than the commission rate for new business.
Accelerators provide an additional incentive for account executives to exceed quota, by applying a multiple onto their commission rate. e.g., 1.25, 1.5, 2.0, etc.
In startups where there isn't product market fit yet or the market is early and revenue is choppy and unpredictable, the startup may consider using a commission rate that is higher than the industry standard. This is to incentivize the account executive to take on the risk of selling a product that may not be fully developed or proven in the market.
Sales Performance Incentive Funds (SPIFs) are a good way to incentivize account executives to sell specific products, or to sell to specific customers. SPIFs can be used to drive revenue in a specific quarter, or to drive revenue in a specific market segment.
Sales engineers have on-target-earnings like account executives, but with a higher base salary and lower variable compensation. Variable compensation ranges from 20-30% of OTE (not base salary). In early-stage startups, criteria for variable compensation may be based on MBOs as well as team revenue attainment.
Co-founders and leadership who are not as familiar with sales compensation should know that compensation plans are subject to change and revenue leadership reserves the right to adjust variable compensation based on contribution for any reason such as deal contribution. The terms of the plan can be changed at any time and quarterly or at half-year or annual increments are more typical.
Ramp periods are where a portion of an account executive's variable compensation is guaranteed for a short period of time when they join. The portion declines over time. e.g., 75% first quarter, 50% second quarter, 0% 3rd quarter.
Early stage startups should consider where ramps are financially viable and weigh the pros and cons of ramps as a way to attract and retain talent. Ramps are a good way to attract talent but can be a disincentive to perform if the account executive is not motivated to sell.
Revenue leaders have similar plans to account executives but with employment agreements with severance and change of control clauses with OTE guarantees. There is also higher base pay and significantly larger equity grants generally in the form of stock options. Durations of severance are generally 6-12 months.